Information on EC 4.1.2.10 - (R)-mandelonitrile lyase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY
4.1.2.10
-
RECOMMENDED NAME
GeneOntology No.
(R)-mandelonitrile lyase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(R)-mandelonitrile = cyanide + benzaldehyde
show the reaction diagram
based on the binding geometry, a reaction mechanism is proposed that involves one of the two conserved active site histidine residues acting as a general base abstracting the proton from the cyanohydrin hydroxyl group. Site-directed mutagenesis shows that both active site histidines are required for the reaction to occur
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
carboligation
Prunus pseudoarmeniaca
-
-
cyanohydrin formation
-
-
-
-
cyanohydrin formation
Prunus pseudoarmeniaca
-
-
Henry reaction
-
-
transcyanation
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
amygdalin and prunasin degradation
-
-
Biosynthesis of secondary metabolites
-
-
Cyanoamino acid metabolism
-
-
Metabolic pathways
-
-
vicianin bioactivation
-
-
SYSTEMATIC NAME
IUBMB Comments
(R)-mandelonitrile benzaldehyde-lyase (cyanide-forming)
A variety of enzymes from different sources and with different properties. Some are flavoproteins, others are not. Active towards a number of aromatic and aliphatic hydroxynitriles (cyanohydrins).
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
(R)-(+)-Mandelonitrile lyase
-
-
-
-
(R)-(+)-Mandelonitrile lyase
O24243
-
(R)-(+)-Mandelonitrile lyase
P52706
-
(R)-HNL
B9X0I2
-
(R)-HNL5
-
-
(R)-hydroxynitrile lyase
-
-
(R)-hydroxynitrile lyase
B7VF77
-
(R)-hydroxynitrile lyase
-
-
(R)-hydroxynitrile lyase
-
-
(R)-hydroxynitrile lyase
B9X0I2
-
(R)-hydroxynitrile lyase
Prunus pseudoarmeniaca
-
-
(R)-Mandelonitrile lyase
-
-
-
-
(R)-Mandelonitrile lyase
-
-
(R)-Mandelonitrile lyase
O24243
-
(R)-Oxynitrilase
-
-
-
-
(R)-Oxynitrilase
-
-
(R)-Oxynitrilase
-
-
(R)-Oxynitrilase
-
-
(R)-Oxynitrilase
-
-
(R)-Oxynitrilase
-
-
(R)-PeHNL
-
-
(R)-selective HNL
-
-
AciX9_0562
E8WYN5
locus name
AciX9_0562
E8WYN5
locus name
-
almond oxynitrilase
-
-
cupin 2 conserved barrel domain protein
E8WYN5
-
cupin 2 conserved barrel domain protein
E8WYN5
-
-
cupin 2 domain-containing protein
G9DE15
-
D-alpha-hydroxynitrile lyase
-
-
-
-
D-Hydroxynitrile lyase
-
-
-
-
D-Oxynitrilase
-
-
-
-
EjHNL
B7VF77
-
FAD-HNL
O24243
-
HNL2
B9X0I1
-
HNL2
B9X0I2
isoform
Hydroxynitrile lyase
-
-
-
-
Hydroxynitrile lyase
-
-
Hydroxynitrile lyase
O24243
-
Hydroxynitrile lyase
Prunus sp.
-
-
Lyase, mandelonitrile
-
-
-
-
mandelonitrile lyase
-
-
MDL
-
-
-
-
Mdl1
O24243
-
Oxynitrilase
-
-
-
-
Oxynitrilase
-
-
Oxynitrilase
-
-
PaHNL
O24243
-
PaHNL1
O24243
-
PaHNL5
-
-
PaHNL5
-
isoenzyme 5
PaHNL5
-
recombinant
PaMDL
O24243
-
PhaMDL
-
-
-
-
PmHNL
-
-
R-hydroxynitrile lyase
-
-
R-selective HNL
Q9LFT6
-
R-selective hydroxynitrile lyase
-
-
R-selective hydroxynitrile lyase
Q9LFT6
-
R-selective hydroxynitrile lyase
-
-
CAS REGISTRY NUMBER
COMMENTARY
9024-43-5
-
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-4-hydroxymandelonitrile
cyanide + 4-hydroxybenzaldehyde
show the reaction diagram
-
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
-
-
-
-
?
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
-
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
-
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
O24243
-
-
-
?
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
-
-
-
-
?
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
Prunus pseudoarmeniaca
-
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
G9DE15
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
E8WYN5
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
Prunus amygdalus turcomanica
-
-
-
-
?
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
-
in a large number of plant species hydroxynitrile lyases catalyzes the decomposition of cyanohydrins in order to generate hydrogen cyanide upon tissue damage. Hydrogen cyanide serves as a deterrent against herbivores and fungi
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
P52706
in Prunus serotina Ehrh. macerates, the cyanogenic diglucoside (R)-amygdalin undergoes stepwise degradation to HCN catalyzed by amygdalin hydrolase, prunasin hydrolase, and (R)-(+)-mandelonitrile lyase
-
-
?
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
-
modeling studies provide insights into the mechanism of cyanogenesis
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
E8WYN5
-
-
-
r
2-chlorobenzaldehyde + HCN
(R)-2-chloromandelonitrile
show the reaction diagram
-
-
after 96 h, 100% yield, 21% enantiomeric excess
-
?
2-chlorobenzaldehyde + nitromethane
1-(2-chlorophenyl)-2-nitroethanol
show the reaction diagram
-
-
34% yield after 2 h
-
?
2-heptanone + HCN
(R)-2-heptanone cyanohydrin
show the reaction diagram
-
needs long reaction time (26 h), providing low enantiomeric exess (14%), which supports the fact that methyl ketones of long aliphatic chain are poor substrates
-
-
?
2-methoxybenzaldehyde + nitromethane
1-(2-methoxyphenyl)-2-nitroethanol
show the reaction diagram
-
-
13% yield after 2 h
-
?
2-methylbenzaldehyde + nitromethane
1-(2-methylphenyl)-2-nitroethanol
show the reaction diagram
-
-
12% yield after 2 h
-
?
3,4-dihydroxybenzaldehyde + HCN
(R)-3,4-dihydroxymandelonitrile
show the reaction diagram
-
-
after 96 h, 100% yield, 99% enantiomeric excess
-
?
3-(2-naphthyl)benzaldehyde + nitromethane
(1R)-1-[3-(naphthalen-2-yl)phenyl]-2-nitroethanol
show the reaction diagram
-
-
7% yield after 2 h
-
?
3-chlorobenzaldehyde + nitromethane
1-(3-chlorophenyl)-2-nitroethanol
show the reaction diagram
-
-
17% yield after 2 h
-
?
3-methoxybenzaldehyde + nitromethane
1-(3-methoxyphenyl)-2-nitroethanol
show the reaction diagram
-
-
17% yield after 2 h
-
?
3-methylbenzaldehyde + nitromethane
1-(3-methylphenyl)-2-nitroethanol
show the reaction diagram
-
-
12% yield after 2 h
-
?
3-phenylpropionaldehyde + HCN
(R)-2-hydroxy-4-phenylbutyronitrile
show the reaction diagram
-
-
after 96 h, 83% yield, 91% enantiomeric excess
-
?
4-bromobenzaldehyde + HCN
(R)-4-bromomandelonitrile
show the reaction diagram
-
-
after 96 h, 100% yield, 99% enantiomeric excess
-
?
4-bromobenzaldehyde + nitromethane
1-(4-bromophenyl)-2-nitroethanol
show the reaction diagram
-
-
20% yield after 2 h
-
?
4-chlorobenzaldehyde + nitromethane
1-(4-chlorophenyl)-2-nitroethanol
show the reaction diagram
-
-
9% yield after 2 h
-
?
4-fluorobenzaldehyde + HCN
(R)-4-fluoroonitrile
show the reaction diagram
-
-
after 96 h, 100% yield, 72% enantiomeric excess
-
?
4-fluorobenzaldehyde + nitromethane
1-(4-fluorophenyl)-2-nitroethanol
show the reaction diagram
-
-
9% yield after 2 h
-
?
4-methoxybenzaldehyde + nitromethane
1-(4-methoxyphenyl)-2-nitroethanol
show the reaction diagram
-
-
2% yield after 2 h
-
?
4-methylbenzaldehyde + nitromethane
1-(4-methylphenyl)-2-nitroethanol
show the reaction diagram
-
-
11% yield after 2 h
-
?
4-nitrobenzaldehyde + HCN
(R)-4-nitromandelonitrile
show the reaction diagram
-
-
after 96 h, 100% yield, 14% enantiomeric excess
-
?
acetyltrimethylsilane + acetone cyanohydrin
?
show the reaction diagram
-
both acetyltrimethylsilane conversion and enantiomeric excess of the product are above 99%
-
-
?
benzaldehyde + HCN
(R)-mandelonitrile
show the reaction diagram
-
-
after 96 h, 100% yield, 99% enantiomeric excess
-
?
benzaldehyde + nitromethane
(R)-2-nitro-1-phenylethanol
show the reaction diagram
-
-
30% yield after 2 h
-
?
cyanide + (2E)-3-methylpent-2-enal
(2R,3E)-2-hydroxy-4-methylhex-3-enenitrile
show the reaction diagram
-
-
-
-
?
cyanide + (2E)-hex-2-enal
(2R,3E)-2-hydroxyhept-3-enenitrile
show the reaction diagram
-
-
-
-
?
cyanide + (2E)-hex-2-enal
(3E)-2-hydroxyhept-3-enenitrile
show the reaction diagram
Q9LFT6
-
53% enantiomeric excess
-
?
cyanide + (2E,4E)-hexa-2,4-dienal
(2R,3E,5E)-2-hydroxyhepta-3,5-dienenitrile
show the reaction diagram
-
-
-
-
?
cyanide + (4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
(2S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
show the reaction diagram
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde is converted to 47.1% (2S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 52.9% (2R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
?
cyanide + (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde
(2S)-hydroxy-[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile + (2R)-hydroxy-[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
show the reaction diagram
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde is converted to 34.2% (2S)-hydroxy[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile and 65.8% (2R)-hydroxy[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
-
?
cyanide + (4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde
(2S)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
show the reaction diagram
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde is converted to 48.2% (2S)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 51.8% (2R)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
?
cyanide + (4S)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
(2S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
show the reaction diagram
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4S)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde is converted to 66.4% (2S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 33.6% (2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
?
cyanide + (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde
(2S)-hydroxy-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile + (2R)-hydroxy-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
show the reaction diagram
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde is converted to 52.6% (2S)-hydroxy[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile and 47.4% (2R)-hydroxy[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
-
?
cyanide + (4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde
(2S)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
show the reaction diagram
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde is converted to 49.3% (2S)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 50.7% (2R)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
?
cyanide + (benzyloxy)acetaldehyde
(2R)-3-(benzyloxy)-2-hydroxypropanenitrile + (2S)-3-(benzyloxy)-2-hydroxypropanenitrile
show the reaction diagram
-
-
43.9% (2S)-3-(benzyloxy)-2-hydroxypropanenitrile and 53.1% (2S)-3-(benzyloxy)-2-hydroxypropanenitrile
-
?
cyanide + 1,4-dioxaspiro[4.5]decane-2-carbaldehyde
(S)-2-hydroxy-2-((R)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile + (R)-2-hydroxy-2-((R)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile + (S)-2-hydroxy-2-((S)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile + (R)-2-hydroxy-2-((S)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile
show the reaction diagram
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate 1,4-dioxaspiro[4.5]decane-2-carbaldehyde is converted to 21.8% (2S)-(2R)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile, 28.3% (2R)-(2R)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile, 30.3% (2S)-(2S)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile and 19.6% (2R)-(2S)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile
-
?
cyanide + 1-phenylethanone
(2R)-2-hydroxy-2-phenylpropanenitrile
show the reaction diagram
-
-
-
-
r
cyanide + 1-phenylethanone
(2R)-2-hydroxy-2-phenylpropanenitrile
show the reaction diagram
-
-
-
-
?
cyanide + 2,2-dimethylpropanal
(2R)-2-hydroxy-3,3-dimethylbutanenitrile
show the reaction diagram
-
activity is 33% of the activity with benzaldehyde
9% enentiomeric excess
-
?
cyanide + 2-(benzyloxy)-3-phenylpropanal
(2S,3S)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile + (2R,3S)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile + (2S,3R)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile + (2R,3R)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile
show the reaction diagram
-
-
26.9% (2S,3S)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile, 23.4% (2R,3S)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile, 29.2% (2S,3R)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile and 20.6% (2R,3R)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile
-
?
cyanide + 2-(benzyloxy)propanal
(2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile + (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile + (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile + (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile
show the reaction diagram
-
-
45.4% (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile, 8.1% (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile, 33.3% (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile and 13.3% (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile
-
?
cyanide + 2-(naphthalen-2-yl)propanal
(2S,3S)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile + (2S,3R)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile + (2R,3S)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile + (2R,3R)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile
show the reaction diagram
-
-
30.4% (2S,3S)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile, 24.0% (2S,3R)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile, 20.0% (2R,3S)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile and 25.6% (2R,3R)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile
-
?
cyanide + 2-bromobenzaldehyde
(2R)-(2-bromophenyl)(hydroxy)ethanenitrile
show the reaction diagram
Q9LFT6
-
98% enantiomeric excess
-
?
cyanide + 2-chlorobenzaldehyde
(2R)-(2-chlorophenyl)(hydroxy)ethanenitrile
show the reaction diagram
Q9LFT6
-
99% enantiomeric excess
-
?
cyanide + 2-chlorobenzaldehyde
(2R)-(2-chlorophenyl)(hydroxy)ethanenitrile
show the reaction diagram
-
-
15.8% yield and 66% enantiomeric excess after 2 h
-
?
cyanide + 2-chlorobenzaldehyde
(R)-2-chloromandelonitrile
show the reaction diagram
-
-
-
-
r
cyanide + 2-chlorobenzaldehyde
(R)-2-chloromandelonitrile
show the reaction diagram
Prunus amygdalus turcomanica
-
-
-
-
?
cyanide + 2-fluorobenzaldehyde
(2R)-(2-fluorophenyl)(hydroxy)ethanenitrile
show the reaction diagram
Q9LFT6
-
99% enantiomeric excess
-
?
cyanide + 2-iodobenzaldehyde
(2R)-(2-iodophenyl)(hydroxy)ethanenitrile
show the reaction diagram
Q9LFT6
-
more than 95% enantiomeric excess
-
?
cyanide + 2-methoxy-3-phenylpropanal
(2S,3S)-2-hydroxy-3-methoxy-4-phenylbutanenitrile + (2R,3S)-2-hydroxy-3-methoxy-4-phenylbutanenitrile + (2S,3R)-2-hydroxy-3-methoxy-4-phenylbutanenitrile + (2R,3R)-2-hydroxy-3-methoxy-4-phenylbutanenitrile
show the reaction diagram
-
-
43.1% (2S,3S)-2-hydroxy-3-methoxy-4-phenylbutanenitrile, 8.4 (2R,3S)-2-hydroxy-3-methoxy-4-phenylbutanenitrile, 40.1% (2S,3R)-2-hydroxy-3-methoxy-4-phenylbutanenitrile and 8.4% (2R,3R)-2-hydroxy-3-methoxy-4-phenylbutanenitrile
-
?
cyanide + 2-methylpropanal
(2R)-2-hydroxy-3-methylbutanenitrile
show the reaction diagram
-
activity is 67% of the activity with benzaldehyde
13% enentiomeric excess
-
?
cyanide + 2-naphthaldehyde
(R)-2-hydroxy-2-(naphthalen-2-yl)acetonitrile
show the reaction diagram
B7VF77
-
-
-
?
cyanide + 2-phenylpropanal
(2R,3S)-2-hydroxy-3-phenylbutanenitrile + (2S,3R)-2-hydroxy-3-phenylbutanenitrile + (2R,3R)-2-hydroxy-3-phenylbutanenitrile
show the reaction diagram
-
-
3.0% (2S,3S)-2-hydroxy-3-phenylbutanenitrile, 51.8% (2R,3S)-2-hydroxy-3-phenylbutanenitrile, 27.6% (2S,3R)-2-hydroxy-3-phenylbutanenitrile and + 17.6% (2R,3R)-2-hydroxy-3-phenylbutanenitrile
-
?
cyanide + 3,4-dihydro-1H-isochromene-3-carbaldehyde
(S)-2-hydroxy-2-((S)-isochroman-3-yl)acetonitrile + (S)-2-hydroxy-2-((R)-isochroman-3-yl)acetonitrile + (R)-2-hydroxy-2-((S)-isochroman-3-yl)acetonitrile + (R)-2-hydroxy-2-((R)-isochroman-3-yl)acetonitrile
show the reaction diagram
-
-
28.6% (2S)-(3S)-3,4-dihydro-1H-isochromen-3-yl(hydroxy)ethanenitrile, 21.5% (2R)-(3S)-3,4-dihydro-1H-isochromen-3-yl(hydroxy)ethanenitrile, 28.7% (2S)-(3R)-3,4-dihydro-1H-isochromen-3-yl(hydroxy)ethanenitrile and 21.1% (2R)-(3R)-3,4-dihydro-1H-isochromen-3-yl(hydroxy)ethanenitrile
-
?
cyanide + 3,4-dihydroxybenzaldehyde
(R)-3,4-dihydroxymandelonitrile
show the reaction diagram
Prunus amygdalus turcomanica
-
-
-
-
?
cyanide + 3-bromobenzaldehyde
(2R)-(3-bromophenyl)(hydroxy)ethanenitrile
show the reaction diagram
Q9LFT6
-
95% enantiomeric excess
-
?
cyanide + 3-chlorobenzaldehyde
(2R)-(3-chlorophenyl)(hydroxy)ethanenitrile
show the reaction diagram
Q9LFT6
-
more than 99% enantiomeric excess
-
?
cyanide + 3-fluorobenzaldehyde
(2R)-(3-fluorophenyl)(hydroxy)ethanenitrile
show the reaction diagram
Q9LFT6
-
more than 99% enantiomeric excess
-
?
cyanide + 3-hydroxy-2,2-dimethylpropanal
(2R)-2,5-dihydroxy-3,3-dimethylpentanenitrile
show the reaction diagram
-
i.e. hydroxypivaldehyde
best enantiomeric excess is obtained at pH 2.5
-
?
cyanide + 3-iodobenzaldehyde
(2R)-(3-iodophenyl)(hydroxy)ethanenitrile
show the reaction diagram
Q9LFT6
-
93% enantiomeric excess
-
?
cyanide + 3-methoxy-3-phenylpropanal
(2S,4S)-2-hydroxy-4-methoxy-4-phenylbutanenitrile + (2R,4S)-2-hydroxy-4-methoxy-4-phenylbutanenitrile + (2S,4R)-2-hydroxy-4-methoxy-4-phenylbutanenitrile + (2R,4R)-2-hydroxy-4-methoxy-4-phenylbutanenitrile
show the reaction diagram
-
-
6.5% (2S,4S)-2-hydroxy-4-methoxy-4-phenylbutanenitrile, 45.2% (2R,4S)-2-hydroxy-4-methoxy-4-phenylbutanenitrile, 14.0% (2S,4R)-2-hydroxy-4-methoxy-4-phenylbutanenitrile, 34.3% (2R,4R)-2-hydroxy-4-methoxy-4-phenylbutanenitrile
-
?
cyanide + 3-phenoxybenzaldehyde
(2R)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
show the reaction diagram
Q9LFT6
-
more than 95% enantiomeric excess
-
?
cyanide + 3-phenoxypropanal
(2R)-2-hydroxy-5-phenylpentanenitrile
show the reaction diagram
-
-
74.3% (2R)-2-hydroxy-5-phenylpentanenitrile and 25.7% (2S)-2-hydroxy-5-phenylpentanenitrile
-
?
cyanide + 3-phenylpropanal
(2R)-2-hydroxy-4-phenylbutanenitrile
show the reaction diagram
Q9LFT6
-
68% enantiomeric excess
-
?
cyanide + 3-tetrahydrothiophenone
(S)-3-hydroxytetrahydrothiophene-3-carbonitrile
show the reaction diagram
-
the enzyme, that shows (R)-stereospecificity for its natural substrate shows S-stereselectivity with the heterocyclic ketone as substrate
-
-
?
cyanide + 4-bromobenzaldehyde
(2R)-(4-bromophenyl)(hydroxy)ethanenitrile
show the reaction diagram
Q9LFT6
-
more than 99% enantiomeric excess
-
?
cyanide + 4-chlorobenzaldehyde
(2R)-(4-chlorophenyl)(hydroxy)ethanenitrile
show the reaction diagram
Q9LFT6
-
more than 99% enantiomeric excess
-
?
cyanide + 4-fluorobenzaldehyde
(2R)-(4-fluorophenyl)(hydroxy)ethanenitrile
show the reaction diagram
Q9LFT6
-
more than 99% enantiomeric excess
-
?
cyanide + 4-hydroxybenzaldehyde
(2R)-(4-hydroxyphenyl)(hydroxy)ethanenitrile
show the reaction diagram
Q9LFT6
-
97% enantiomeric excess
-
?
cyanide + 4-hydroxybenzaldehyde
(R)-4-hydroxymandelonitrile
show the reaction diagram
-
-
-
-
r
cyanide + 4-hydroxybutanal
(R)-2,5-dihydroxypentanenitrile
show the reaction diagram
-
by varying the different reaction parameters it is possible to reduce the extension of the undesirable non-enzymatic competing reactions and optimize the optical purity of the cyanohydrin product. Best results are obtained at 15C
-
-
?
cyanide + 4-iodobenzaldehyde
(2R)-(4-iodophenyl)(hydroxy)ethanenitrile
show the reaction diagram
Q9LFT6
-
92% enantiomeric excess
-
?
cyanide + 4-methoxybenzaldehyde
(2R)-(4-methoxyphenyl)(hydroxy)ethanenitrile
show the reaction diagram
Q9LFT6
-
68% enantiomeric excess
-
?
cyanide + 4-methoxybenzaldehyde
(2R)-hydroxy(4-methoxyphenyl)ethanenitrile
show the reaction diagram
-
-
-
-
r
cyanide + 4-methoxybenzaldehyde
(2R)-hydroxy(4-methoxyphenyl)ethanenitrile
show the reaction diagram
-
-
-
-
?
cyanide + 4-phenylbutan-2-one
2-hydroxy-4-phenylbutyronitrile
show the reaction diagram
Prunus amygdalus turcomanica
-
-
-
-
?
cyanide + 4-phenylbutanal
(2R)-2-hydroxy-5-phenylpentanenitrile
show the reaction diagram
-
-
88.9% (2R)-2-hydroxy-5-phenylpentanenitrile and 11.1% (2S)-2-hydroxy-5-phenylpentanenitrile
-
?
cyanide + 5-hydroxypentanal
(R)-2,6-dihydroxyhexanenitrile
show the reaction diagram
-
by varying the different reaction parameters it is possible to reduce the extension of the undesirable non-enzymatic competing reaction and optimize the optical purity of the cyanohydrin product. Best results are obtained at 15C
-
-
?
cyanide + 6-methylhept-5-en-2-one
(2R)-2-hydroxy-2,6-dimethylhept-5-enenitrile
show the reaction diagram
Q9LFT6
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
-
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
Prunus sp.
-
-
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
B9X0I1, B9X0I2
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
-
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
B7VF77
-
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
-
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
B9X0I1, B9X0I2
-
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
Prunus pseudoarmeniaca
-
-
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
Prunus amygdalus turcomanica
-
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
-
-
more than 99% enantiomeric excess
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
-
-
more than 99% enantiomeric excess
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
Q9LFT6
-
more than 99% enantiomeric excess
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
-
-
82% yield, 99% enantiomeric excess
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
-
-
90.3% yield and 100% enantiomeric excess after 2 h
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
O24243
-
99% yield, 99% enantiomeric excess
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
E8WYN5
-
90% enantiomeric excess at 80% conversion using 0.5 M benzaldehyde in a biphasic reaction system with methyl tertiary butyl ether
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
G9DE15
-
preference for (R)-product of 28%
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
Prunus sp.
-
(R)-specific
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
-
both pH and temperature have a large effect on the initial velocity and enantiomeric excess (e.e.) of the product, (R)-mandelonitrile. High enantiomeric purity of the product is observed at low pH and temperature because the non-enzymatic reaction producing racemates of mandelonitrile is almost suppressed. The optimum pH and temperature to obtain high enantiomeric excess are pH 4.0 and 10C, respectively. The best solvent for the highest initial velocity and enantiomeric excess is diethyl ether with an optimum aqueous phase content of 50% (v/v). The initial reaction rate increases as the aqueous phase content rises, but when the content is more than 50%, a reduction of enantiomeric excess is observed. Increasing the concentration of the substrates accelerates the initial velocity, but causes a slight decrease in the e.e. of the product. Under the optimized conditions, the conversion and enantiomeric excess of (R)-mandelonitrile for 3 h are 40 and 99%, respectively
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
-
several parameters influence the enantiomeric purity of the product and initial velocity of the reaction. Both pH and temperature are important parameters controlling the enantiomeric purity of the product. The optimum pH and temperature are pH 4 and 10C, respectively. At the optimum pH and temperature, the spontaneous non-enzymatic reaction yielding the racemic mandelonitrile is almost completely suppressed. The initial velocity is markedly affected by the type of organic solvent in the biphasic system, while high enantiomeric purity is obtained when organic solvents having log P lower than 3.5 are used. The highest initial velocity of reaction and enantiomeric purity of (R)-mandelonitrile are obtained in the biphasic system of dibutyl ether with the aqueous phase content of 30% (v/v). The optimum substrate concentrations are 250 mM for benzaldehyde and 900 mM for acetone cyanohydrin, and the optimum enzyme concentration is 26.7 units/ml. The highest enantiomeric purity of (R)-mandelonitrile is successfully obtained with conversion and enantiomeric excess of 31.6% and 98.6%, respectively
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
-
the formation of (R)-mandelonitrile from benzaldehyde and cyanide catalyzed by Prunus amygdalus hydroxynitrile lyase is chosen as a model reaction for the development and validation of a process model for production of (R)-cyanohydrins in an aqueous-organic biphasic-stirred tank reactor with an unknown interfacial area operated in batch mode. At 5C and pH 5.5 the nonenzymatic reaction towards rac-mandelonitrile is largely suppressed
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
E8WYN5
-
90% enantiomeric excess at 80% conversion using 0.5 M benzaldehyde in a biphasic reaction system with methyl tertiary butyl ether
-
r
cyanide + butanal
(2R)-2-hydroxypentanenitrile
show the reaction diagram
O24243
-
100% yield, 90% enantiomeric excess
-
?
cyanide + butanal
(2R)-2-hydroxypentanenitrile
show the reaction diagram
-
-
42% yield, 55% enantiomeric excess
-
?
cyanide + cinnamaldehyde
(2R,3E)-2-hydroxy-4-phenylbut-3-enenitrile
show the reaction diagram
-
i.e. (2E)-3-phenylprop-2-enal
-
-
?
cyanide + cyclohexanecarbaldehyde
(2R)-cyclohexyl(hydroxy)acetonitrile
show the reaction diagram
-
activity is 41% of the activity with benzaldehyde
10% enentiomeric excess
-
?
cyanide + cyclohexanone
1-hydroxycyclohexanecarbonitrile
show the reaction diagram
Q9LFT6
-
-
-
?
cyanide + decanal
(2R)-2-hydroxyundecanal
show the reaction diagram
Q9LFT6
-
56% enantiomeric excess
-
?
cyanide + furan-2-carbaldehyde
(2R)-furan-2-yl(hydroxy)ethanenitrile
show the reaction diagram
-
-
-
-
r
cyanide + furan-2-carbaldehyde
(2R)-furan-2-yl(hydroxy)ethanenitrile
show the reaction diagram
-
-
-
-
?
cyanide + hexan-2-one
(2R)-2-hydroxy-2-methylhexanenitrile
show the reaction diagram
-
-
-
-
r
cyanide + hexan-2-one
(2R)-2-hydroxy-2-methylhexanenitrile
show the reaction diagram
-
-
-
-
?
cyanide + hexan-2-one
(2R)-2-hydroxy-2-methylhexanenitrile
show the reaction diagram
Q9LFT6
-
95% enantiomeric excess
-
?
cyanide + hexanal
(2R)-2-hydroxyheptanenitrile
show the reaction diagram
Q9LFT6
-
98% enantiomeric excess
-
?
cyanide + isobutyraldehyde
2-hydroxy-3-methylbutyronitrile
show the reaction diagram
B7VF77
-
-
-
?
cyanide + naphthalen-2-ylacetaldehyde
(2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
show the reaction diagram
-
-
3.5% (2S)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile and 96.5% (2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
-
?
cyanide + naphthalen-2-ylacetaldehyde
(2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile + (2S)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
show the reaction diagram
-
-
33.2% (2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile and 66.8% (2S)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
-
?
cyanide + naphthalene-2-carbaldehyde
(2R)-hydroxy(naphthalen-2-yl)ethanenitrile
show the reaction diagram
-
-
97.6% (2R)-hydroxy(naphthalen-2-yl)ethanenitrile and 2.4% (2S)-hydroxy(naphthalen-2-yl)ethanenitrile
-
?
cyanide + p-anisaldehyde
(R)-2-hydroxy-2-(4-methoxyphenyl)acetonitrile
show the reaction diagram
B7VF77
-
-
-
?
cyanide + pentan-2-one
(2R)-2-hydroxy-2-methylpentanenitrile
show the reaction diagram
O24243
-
-
-
?
cyanide + pentan-2-one
(2R)-2-hydroxy-2-methylpentanenitrile
show the reaction diagram
-
-
17% yield
-
?
cyanide + phenylacetaldehyde
(2R)-2-hydroxy-3-phenylpropanenitrile
show the reaction diagram
Q9LFT6
-
96% enantiomeric excess
-
?
cyanide + phenylacetaldehyde
(2R)-2-hydroxy-3-phenylpropanenitrile
show the reaction diagram
-
-
96.3% (2R)-2-hydroxy-3-phenylpropanenitrile and 3.7% (2S)-2-hydroxy-3-phenylpropanenitrile
-
?
cyanide + piperonal
(R)-2-hydroxy-2-(3,4-methylenedioxyphenyl)acetonitrile
show the reaction diagram
B7VF77
-
-
-
?
cyanide + pivaldehyde
pivaloyl cyanide
show the reaction diagram
B7VF77
-
-
-
?
cyanide + propanal
(2R)-2-hydroxybutanenitrile
show the reaction diagram
-
activity is 20% of the activity with benzaldehyde
7% enentiomeric excess
-
?
cyanide + propionaldehyde
2-hydroxybutyronitrile
show the reaction diagram
B7VF77
-
-
-
?
cyanide + tetrahydro-2H-pyran-2-carbaldehyde
(2S)-hydroxy-[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile + (2R)-hydroxy-[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile + (2S)-hydroxy-[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile + (2R)-hydroxy-[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile
show the reaction diagram
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate tetrahydro-2H-pyran-2-carbaldehyde is converted to 47.6% (2S)-hydroxy[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile, 4.6% (2R)-hydroxy[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile, 42.6% (2S)-hydroxy[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile and 5.2% (2R)-hydroxy[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile
-
?
cyanide + tetrahydrofuran-2-carbaldehyde
(2S)-hydroxy-[(2R)-tetrahydrofuran-2-yl]ethanenitrile + (2R)-hydroxy-[(2R)-tetrahydrofuran-2-yl]ethanenitrile + (2S)-hydroxy-[(2S)-tetrahydrofuran-2-yl]ethanenitrile + (2R)-hydroxy-[(2S)-tetrahydrofuran-2-yl]ethanenitrile
show the reaction diagram
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate tetrahydrofuran-2-carbaldehyde is converted to 33.7% (2S)-hydroxy[(2R)-tetrahydrofuran-2-yl]ethanenitrile, 16.2% (2R)-hydroxy[(2R)-tetrahydrofuran-2-yl]ethanenitrile, 35.6% (2S)-hydroxy[(2S)-tetrahydrofuran-2-yl]ethanenitrile and 14.5% (2R)-hydroxy[(2S)-tetrahydrofuran-2-yl]ethanenitrile
-
?
cyanide + thiophene-2-carbaldehyde
(2R)-hydroxy(thiophen-2-yl)ethanenitrile
show the reaction diagram
O24243
-
48% yield, 87% enantiomeric excess
-
?
cyanide + thiophene-2-carbaldehyde
(2R)-hydroxy(thiophen-2-yl)ethanenitrile
show the reaction diagram
-
-
87% yield, 99% enentiomeric excess
-
?
cyanide + thiophene-2-carbaldehyde
(2S)-hydroxy(thiophen-2-yl)ethanenitrile
show the reaction diagram
-
activity is 2fold higher than with benzaldehyde
75% enentiomeric excess, The (S)-configuration is due to the Cahn-Ingold-Prelog rules
-
?
cyanide + thiophene-2-carbaldehyde
hydroxy(thiophen-2-yl)ethanenitrile
show the reaction diagram
Q9LFT6
-
separation of enantiomers not posible
-
?
HCN + 1-naphthalenecarboxaldehyde
(R)-2-hydroxy-2-(1-naphthyl)acetonitrile
show the reaction diagram
-
60% conversion
93% enantiomeric excess
-
?
HCN + 2,3,4,5-tetrafluorobenzaldehyde
(R)-2-hydroxy-2-(2,3,4,5-tetrafluorophenyl)acetonitrile
show the reaction diagram
-
26% conversion
23% enantiomeric excess
-
?
HCN + 2,3,4-trimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3,4-trimethoxyphenyl)acetonitrile
show the reaction diagram
-
14% conversion
% enantiomeric excess
-
?
HCN + 2,3,5,6-tetrafluorobenzaldehyde
(R)-2-hydroxy-2-(2,3,5,6-tetrafluorophenyl)acetonitrile
show the reaction diagram
-
21% conversion
12% enantiomeric excess
-
?
HCN + 2,3,5-trimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3,5-trimethoxyphenyl)acetonitrile
show the reaction diagram
-
16% conversion
28% enantiomeric excess
-
?
HCN + 2,3-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,3-dichlorophenyl)acetonitrile
show the reaction diagram
-
11% conversion
22% enantiomeric excess
-
?
HCN + 2,3-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3-dimethoxyphenyl)acetonitrile
show the reaction diagram
-
7% conversion
37% enantiomeric excess
-
?
HCN + 2,4-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,4-dichlorophenyl)acetonitrile
show the reaction diagram
-
13% conversion
78% enantiomeric excess
-
?
HCN + 2,4-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,4-dimethoxyphenyl)acetonitrile
show the reaction diagram
-
11% conversion
48% enantiomeric excess
-
?
HCN + 2,4-dimethylbenzaldehyde
(R)-2-hydroxy-2-(2,4-dimethylphenyl)acetonitrile
show the reaction diagram
-
5.8% conversion
86% enantiomeric excess
-
?
HCN + 2,5-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,5-dichlorophenyl)acetonitrile
show the reaction diagram
-
8.8% conversion
57% enantiomeric excess
-
?
HCN + 2,5-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,5-dimethoxyphenyl)acetonitrile
show the reaction diagram
-
9% conversion
63% enantiomeric excess
-
?
HCN + 2,6-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,6-dichlorophenyl)acetonitrile
show the reaction diagram
-
10% conversion
12% enantiomeric excess
-
?
HCN + 2,6-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,6-dimethoxyphenyl)acetonitrile
show the reaction diagram
-
6.5% conversion
32% enantiomeric excess
-
?
HCN + 2-allylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-allylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-allylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-allylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-allyloxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-allyloxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-allyloxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-allyloxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-butanone
(R)-2-hydroxy-2-methylbutyronitrile
show the reaction diagram
-
48% conversion
72% enantiomeric excess
-
?
HCN + 2-chlorobenzaldehyde
(R)-2-hydroxy-2-(2-chlorophenyl)acetonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-chlorobenzaldehyde
(R)-2-hydroxy-2-(2-chlorophenyl)acetonitrile
show the reaction diagram
-
37% conversion
56% enantiomeric excess
-
?
HCN + 2-decanone
(R)-2-hydroxy-2-methyl-decanenitrile
show the reaction diagram
-
18% conversion
52% enantiomeric excess
-
?
HCN + 2-ethoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-ethoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-ethoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-ethoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-ethylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-ethylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-ethylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-methylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-furancarboxaldehyde
(S)-2-hydroxy-2-(2-furyl)acetonitrile
show the reaction diagram
-
1.2% conversion
98% enantiomeric excess
-
?
HCN + 2-heptanone
(R)-2-hydroxy-2-methyl-heptanenitrile
show the reaction diagram
-
39% conversion
74% enantiomeric excess
-
?
HCN + 2-hexanone
(R)-2-hydroxy-2-methyl-hexanenitrile
show the reaction diagram
-
48% conversion
80% enantiomeric excess
-
?
HCN + 2-methoxybenzaldehyde
(R)-2-hydroxy-2-(2-methoxyphenyl)acetonitrile
show the reaction diagram
-
6.0% conversion
41% enantiomeric excess
-
?
HCN + 2-methoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-methoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-methoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-methoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-methylbenzaldehyde
(R)-2-hydroxy-2-(2-methylphenyl)acetonitrile
show the reaction diagram
-
6% conversion
61% enantiomeric excess
-
?
HCN + 2-methylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-methylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-methylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-methylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-n-propoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-n-propoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-n-propoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-n-propoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-n-propylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-n-propylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-n-propylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-n-propylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-naphthalenecarboxaldehyde
(R)-2-hydroxy-2-(2-naphthyl)acetonitrile
show the reaction diagram
-
58% conversion
98% enantiomeric excess
-
?
HCN + 2-nonanone
(R)-2-hydroxy-2-methyl-nonanenitrile
show the reaction diagram
-
20% conversion
65% enantiomeric excess
-
?
HCN + 2-octanone
(R)-2-hydroxy-2-methyl-octanenitrile
show the reaction diagram
-
22% conversion
67% enantiomeric excess
-
?
HCN + 2-pentanone
(R)-2-hydroxy-2-methyl-pentanenitrile
show the reaction diagram
-
46% conversion
81% enantiomeric excess
-
?
HCN + 2-pyridinecarboxyaldehyde
(S)-2-hydroxy-2-(2-pyridyl)acetonitrile
show the reaction diagram
-
89% conversion
22% enantiomeric excess
-
?
HCN + 2-quinolinecarboxaldehyde
(S)-2-hydroxy-2-(2-quinolinyl)acetonitrile
show the reaction diagram
-
38% conversion
21% enantiomeric excess
-
?
HCN + 2-thiophenecarboxaldehyde
(S)-2-hydroxy-2-(2-thiophenyl)acetonitrile
show the reaction diagram
-
31% conversion
88% enantiomeric excess
-
?
HCN + 2-trifluoromethylbenzaldehyde
(R)-2-hydroxy-2-(2-trifluoromethylphenyl)acetonitrile
show the reaction diagram
-
72% conversion
5% enantiomeric excess
-
?
HCN + 2-undecanone
(R)-2-hydroxy-2-methyl-undecanenitrile
show the reaction diagram
-
21% conversion
31% enantiomeric excess
-
?
HCN + 3,3-dimethyl-2-butanone
(R)-2-hydroxy-2,3,3-trimethyl-butyronitrile
show the reaction diagram
-
28% conversion
38% enantiomeric excess
-
?
HCN + 3,4,5-trimethoxybenzaldehyde
(R)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)acetonitrile
show the reaction diagram
-
24% conversion
31% enantiomeric excess
-
?
HCN + 3,4-dichlorobenzaldehyde
(R)-2-hydroxy-2-(3,4-dichlorophenyl)acetonitrile
show the reaction diagram
-
7.9% conversion
94% enantiomeric excess
-
?
HCN + 3,4-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(3,4-dimethoxyphenyl)acetonitrile
show the reaction diagram
-
13% conversion
78% enantiomeric excess
-
?
HCN + 3,5-dichlorobenzaldehyde
(R)-2-hydroxy-2-(3,5-dichlorophenyl)acetonitrile
show the reaction diagram
-
21% conversion
92% enantiomeric excess
-
?
HCN + 3,5-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(3,5-dimethoxyphenyl)acetonitrile
show the reaction diagram
-
17% conversion
97% enantiomeric excess
-
?
HCN + 3-chlorobenzaldehyde
(R)-2-hydroxy-2-(3-chlorophenyl)acetonitrile
show the reaction diagram
-
38% conversion
92% enantiomeric excess
-
?
HCN + 3-methoxybenzaldehyde
(R)-2-hydroxy-2-(3-methoxyphenyl)acetonitrile
show the reaction diagram
-
31% conversion
92% enantiomeric excess
-
?
HCN + 3-methoxycyclohexanone
cis-(1R,3S)-1-hydroxy-3-methoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 3-methoxycyclohexanone
trans-(1R,3R)-1-hydroxy-3-methoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 3-methyl-2-butanone
(R)-2-hydroxy-2,3-dimethyl-butyronitrile
show the reaction diagram
-
39% conversion
42% enantiomeric excess
-
?
HCN + 3-methylbenzaldehyde
(R)-2-hydroxy-2-(3-methylphenyl)acetonitrile
show the reaction diagram
-
7.5% conversion
87% enantiomeric excess
-
?
HCN + 3-methylcyclohexanone
cis-(1R,3S)-1-hydroxy-3-methylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 3-methylcyclohexanone
trans-(1R,3R)-1-hydroxy-3-methylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 3-nitrobenzaldehyde
(R)-2-hydroxy-2-(3-nitrophenyl)acetonitrile
show the reaction diagram
-
87% conversion
65% enantiomeric excess
-
?
HCN + 3-phenoxybenzaldehyde
(R)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
show the reaction diagram
-
42% conversion
more than 99% enantiomeric excess
-
?
HCN + 3-pyridinecarboxyaldehyde
(R)-2-hydroxy-2-(3-pyridyl)acetonitrile
show the reaction diagram
-
90% conversion
75% enantiomeric excess
-
?
HCN + 3-trifluoromethylbenzaldehyde
(R)-2-hydroxy-2-(3-trifluoro-methylphenyl)acetonitrile
show the reaction diagram
-
91% conversion
68% enantiomeric excess
-
?
HCN + 3-trifluoromethylcyclohexanone
cis-(1R,3S)-1-hydroxy-3-trifluoromethylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 3-trifluoromethylcyclohexanone
trans-(1R,3R)-1-hydroxy-3-trifluoromethylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 4-allyloxybenzaldehyde
(R)-2-hydroxy-2-(4-allyloxyphenyl)acetonitrile
show the reaction diagram
-
6.4% conversion
98% enantiomeric excess
-
?
HCN + 4-benzyloxybenzaldehyde
(R)-2-hydroxy-2-(4-benzyloxyphenyl)acetonitrile
show the reaction diagram
-
5.8% conversion
98% enantiomeric excess
-
?
HCN + 4-bromobenzaldehyde
(R)-2-hydroxy-2-(4-bromophenyl)acetonitrile
show the reaction diagram
-
22% conversion
99% enantiomeric excess
-
?
HCN + 4-chlorbenzaldehyde
(R)-2-hydroxy-2-(4-chlorophenyl)acetonitrile
show the reaction diagram
G9DE15
-
-
-
?
HCN + 4-chlorbenzaldehyde
(R)-2-hydroxy-2-(4-chlorophenyl)acetonitrile
show the reaction diagram
-
21% conversion
99% enantiomeric excess
-
?
HCN + 4-fluorobenzaldehyde
(R)-2-hydroxy-2-(4-fluorophenyl)acetonitrile
show the reaction diagram
-
28% conversion
% enantiomeric excess
-
?
HCN + 4-methoxybenzaldehyde
(R)-2-hydroxy-2-(4-methoxyphenyl)acetonitrile
show the reaction diagram
-
17% conversion
97% enantiomeric excess
-
?
HCN + 4-methyl-2-pentanone
(R)-2-hydroxy-2,4-dimethyl-pentanenitrile
show the reaction diagram
-
40% conversion
88% enantiomeric excess
-
?
HCN + 4-methylbenzaldehyde
(R)-2-hydroxy-2-(4-methylphenyl)acetonitrile
show the reaction diagram
-
7.0% conversion
95% enantiomeric excess
-
?
HCN + 4-nitrobenzaldehyde
(R)-2-hydroxy-2-(4-nitrophenyl)acetonitrile
show the reaction diagram
-
89% conversion
71% enantiomeric excess
-
?
HCN + 4-phenoxybenzaldehyde
(R)-2-hydroxy-2-(4-phenoxyphenyl)acetonitrile
show the reaction diagram
G9DE15
-
-
-
?
HCN + 4-pyridinecarboxyaldehyde
(R)-2-hydroxy-2-(4-pyridyl)acetonitrile
show the reaction diagram
-
65% conversion
41% enantiomeric excess
-
?
HCN + 4-quinolinecarboxaldehyde
(R)-2-hydroxy-2-(4-quinolinyl)acetonitrile
show the reaction diagram
-
73% conversion
28% enantiomeric excess
-
?
HCN + 4-tert-butyldimethylsilyloxybenzaldehyde
(R)-2-hydroxy-2-(4-tert-butyldimethylsilyloxyphenyl)acetonitrile
show the reaction diagram
-
4.8% conversion
97% enantiomeric excess
-
?
HCN + 4-trifluoromethylbenzaldehyde
(R)-2-hydroxy-2-(4-trifluoromethylphenyl)acetonitrile
show the reaction diagram
-
90% conversion
76% enantiomeric excess
-
?
HCN + 5-methyl-2-hexanone
(R)-2-hydroxy-2,5-dimethyl-hexanenitrile
show the reaction diagram
-
30% conversion
76% enantiomeric excess
-
?
HCN + acetophenone
2-hydroxyphenylpropionitrile
show the reaction diagram
-
-
-
-
?
HCN + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
-
13% conversion
93% enantiomeric excess
-
?
HCN + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
-
reaction in a two phase solvent system aqueous buffer and ionic liquid. When compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remains good
-
-
?
HCN + benzaldehyde
(R)-2-hydroxy-2-phenylacetonitrile
show the reaction diagram
-
-
-
-
?
HCN + butanal
(R)-2-hydroxy-pentanenitrile
show the reaction diagram
-
51% conversion
84% enantiomeric excess
-
?
HCN + cyclohexanecarboxaldehyde
(R)-2-hydroxy-2-cyclohexyl-acetonitrile
show the reaction diagram
-
54% conversion
94% enantiomeric excess
-
?
HCN + cyclopentanecarboxaldehyde
(R)-2-hydroxy-2-cyclopentyl-acetonitrile
show the reaction diagram
-
51% conversion
91% enantiomeric excess
-
?
HCN + decanal
(R)-2-hydroxyundecanenitrile
show the reaction diagram
-
reaction in a two phase solvent system aqueous buffer and ionic liquid. When compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remains good
-
-
?
HCN + dodecanal
(R)-2-hydroxytridecanenitrile
show the reaction diagram
-
reaction in a two phase solvent system aqueous buffer and ionic liquid. When compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remains good
-
-
?
HCN + hexanal
(R)-2-hydroxy-octanenitrile
show the reaction diagram
-
38% conversion
81% enantiomeric excess
-
?
HCN + iso-propoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-iso-propoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + iso-propoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-iso-propoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + isobutyraldehyde
(R)-2-hydroxy-3-methyl-butyronitrile
show the reaction diagram
-
43% conversion
88% enantiomeric excess
-
?
HCN + pentanal
(R)-2-hydroxy-hexanenitrile
show the reaction diagram
-
36% conversion
85% enantiomeric excess
-
?
HCN + piperonal
(R)-2-hydroxy-2-(3,4-methylenedioxyphenyl)acetonitrile
show the reaction diagram
-
34% conversion
98% enantiomeric excess
-
?
HCN + pivaldehyde
(R)-2-hydroxy-3,3-dimethyl-butyronitrile
show the reaction diagram
-
29% conversion
92% enantiomeric excess
-
?
HCN + propanal
(R)-2-hydroxy-butyronitrile
show the reaction diagram
-
48% conversion
78% enantiomeric excess
-
?
HCN + trimethylsilylmethylketone
(R)-2-hydroxy-2-trimethylsilyl-propanenitrile
show the reaction diagram
-
62% conversion
72% enantiomeric excess
-
?
nitromethane + 2-chlorobenzaldehyde
(1R)-1-(2-chlorophenyl)-2-nitroethanol
show the reaction diagram
-
-
34% yield, 68% enantiomeric excess
-
?
nitromethane + 3-methoxybenzaldehyde
(1R)-1-(3-methoxyphenyl)-2-nitroethanol
show the reaction diagram
-
-
17% yield, 91% enantiomeric excess
-
?
nitromethane + 4-fluorobenzaldehyde
(1R)-1-(4-fluorophenyl)-2-nitroethanol
show the reaction diagram
-
-
20% yield, 81% enantiomeric excess
-
?
nitromethane + benzaldehyde
(1R)-2-nitro-1-phenylethanol
show the reaction diagram
-
30% yield, 91% enantiomeric excess
-
-
?
propiophenone + HCN
(S)-1-phenylacetone cyanohydrin
show the reaction diagram
-
with 24% conversion and 46% enantiomeric exess
-
-
?
HCN + undecanal
(R)-2-hydroxydodecanenitrile
show the reaction diagram
-
reaction in a two phase solvent system aqueous buffer and ionic liquid. When compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remains good
-
-
?
additional information
?
-
-
substrates having ortho substituents are poor substrates in terms of enantioselectivity of the resulting cyanohydrins
-
-
-
additional information
?
-
-
biocatalyst to synthesize a series of chiral methyl ketone cyanohydrins with satisfactory conversion and conspicuous enantiomeric excess. 2',6'-dimethylacetophenone, a compound with steric hindrance on the phenyl group is unsuitable as substrate
-
-
-
additional information
?
-
-
activity is less than 5% of the activity with benzaldehyde: 4-methoxybenzaldehyde, naphthalene-1-carbaldehyde, naphthalene-2-carbaldehyde and 1,3-benzodioxole-5-carbaldehyde
-
-
-
additional information
?
-
-
aliphatic carbonyls are poorly converted
-
-
-
additional information
?
-
Q9LFT6
broad substrate range includes alphatic and aromatic aldehydes as well as ketones. Low activity with acetaldehyde, propionaldehyde and acetone cyanohydrin
-
-
-
additional information
?
-
-
low activity towards acetone cyanohydrin
-
-
-
additional information
?
-
-
naphthyl and alkoxy substituents in the alpha- and also in the beta-position to the aldehyde group significantly influence the stereochemical outcome of the oxynitrilase-catalyzed transformation. No activity with methoxy(phenyl)acetaldehyde
-
-
-
additional information
?
-
-
synthesis of optically active (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanide by asymmetric transcyanation of acetyltrimethylsilane with acetone cyanohydrin in a biphasic system. The substrate conversion and the product enantiomeric excess are 95% and 98% under the optimized conditions. Acetyltrimethylsilane was a better substrate of the enzyme than its carbon counterpart
-
-
-
additional information
?
-
-
the enzyme also catalyzes transcyanation of benzaldehyde and acetone cyanohydrin to (R)-mandelonitrile
-
-
-
additional information
?
-
B7VF77
the enzyme is active towards aromatic and aliphatic aldehydes and shows a preference for small substrates over bulky one
-
-
-
additional information
?
-
-
the enzyme does not accept 3,3-dimethyl-2-butanone as substrate
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
-
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
O24243
-
-
-
?
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
-
in a large number of plant species hydroxynitrile lyases catalyzes the decomposition of cyanohydrins in order to generate hydrogen cyanide upon tissue damage. Hydrogen cyanide serves as a deterrent against herbivores and fungi
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
P52706
in Prunus serotina Ehrh. macerates, the cyanogenic diglucoside (R)-amygdalin undergoes stepwise degradation to HCN catalyzed by amygdalin hydrolase, prunasin hydrolase, and (R)-(+)-mandelonitrile lyase
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
-
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
Prunus sp.
-
-
-
-
r
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FAD
-
a flavoprotein
FAD
-
absolute requirement of oxidized FAD as cofactor. Enzyme activity requires the FAD cofactor to be bound in its oxidized form. The observed inactivation upon cofactor reduction is largely caused by the reversal of the electrostatic potential within the active site
FAD
-
FAD-dependent enzyme, the FAD cofactor is deeply buried within the molecule and is completely isolated from bulk solvent
FAD
B7VF77
enzyme is a flavoprotein containing FAD as a prosthetic group
FAD
-
there is no evidence that the flavin cofactor directly participates in the reaction
FAD
B9X0I1, B9X0I2
-
additional information
-
not a flavoprotein
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mn2+
E8WYN5
required
additional information
B7VF77
metal ions are not required for its activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2-Iodoacetamide
B9X0I1, B9X0I2
1 mM, 9% residual activity; 9.0% residual activity at 1 mM
2-mercaptoethanol
B7VF77
10 mM, 19% inhibition
2-mercaptoethanol
B9X0I1, B9X0I2
87.3% residual activity at 1 mM
Ag+
B9X0I1, B9X0I2
1 mM, 8% residual activity; 8.2 residual activity at 1 mM
AgNO3
-
0.2 mM, 85% inhibition
AgNO3
B7VF77
1 mM, 100% inhibition
CuSO4
B7VF77
1 mM, 100% inhibition
diethyl dicarbonate
-
0.5 mM, 60% inhibition
diethyl dicarbonate
-
0.5 mM, 50% inhibition. 2 mM, 79% inhibition
diethyldicarbonate
B7VF77
1 mM, 36% inhibition
diethyldicarbonate
B9X0I1, B9X0I2
35.4% residual activity at 1 mM
diisopropyl fluorophosphate
-
2 mM, 80% inhibition
FeCl3
B7VF77
1 mM, 50% inhibition
Hg2+
B9X0I1, B9X0I2
1 mM, 9% residual activity; 9.0% residual activity at 1 mM
HgCl2
B7VF77
1 mM, 100% inhibition
iodoacetamide
-
2 mM, 70% inhibition
iodoacetic acid
B7VF77
1 mM, 53% inhibition
NH2OH
B9X0I1, B9X0I2
82.7% residual activity at 1 mM
p-chloromercuribenzoic acid
B9X0I1, B9X0I2
58.6% residual activity at 10 mM
phenylmethylsulfonyl fluoride
-
2 mM, 50% inhibition
phenylmethylsulfonyl fluoride
B9X0I1, B9X0I2
68.5% residual activity at 1 mM
Phenylmethylsulfonylfluoride
B7VF77
1 mM, 59% inhibition
iodoacetic acid
B9X0I1, B9X0I2
1 mM, 8% residual activity; 8.0% residual activity at 1 mM
additional information
-
the enzyme is not inhibited by sulfhydryl- or hydroxyl-modifying reagents
-
additional information
-
no inhibition by acetate
-
additional information
B9X0I1, B9X0I2
not inhibited by EDTA, EGTA, sodium fluoride, o-phenanthroline, 2,4-dinitro-1-thiocyanate, NaN3, dithiothreitol, phenylhydrazine, Triton X-100, 2,2'-bipyridyl, N-ethylmaleimide, and D-cycloserine
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
reaction in a two phase solvent system aqueous buffer and ionic liquid. When compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remained good
-
additional information
-
best solvents are diisopropylether, tert-butylmethylether or di-n-butylether. With all the three solvents more than 95% enantioselectivity is observed. However, the rate of the reaction is very slow
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1.4
(R)-4-hydroxymandelonitrile
-
pH 5.0, 25C
0.161
(R)-Mandelonitrile
B7VF77
pH 5.5
0.38
(R)-Mandelonitrile
Prunus amygdalus turcomanica
-
native protein, pH 5.5, 25C
0.95
(R)-Mandelonitrile
Prunus amygdalus turcomanica
-
enzyme immobilized onto Eupergit C250 L, pH 5.5, 25C
1.03
(R)-Mandelonitrile
Prunus pseudoarmeniaca
-
enzyme immobilized onto Eupergit C 250L, in 50 mM citrate buffer, pH 6.0, 25C
1.3
(R)-Mandelonitrile
Prunus amygdalus turcomanica
-
enzyme immobilized onto Eupergit CM, pH 5.5, 25C
1.6
(R)-Mandelonitrile
Prunus pseudoarmeniaca
-
enzyme immobilized onto Eupergit C, in 50 mM citrate buffer, pH 6.0, 25C
2.23
(R)-Mandelonitrile
Prunus pseudoarmeniaca
-
free enzyme, in 50 mM citrate buffer, pH 6.0, 25C
10.3
(R)-Mandelonitrile
E8WYN5
pH 4.5, 25C
1.1
2-naphthaldehyde
B7VF77
pH 5.5
6
4-hydroxybenzaldehyde
-
pH 5.0, 25C
0.83
benzaldehyde
-
pH 5.3
1 - 4
benzaldehyde
Prunus amygdalus turcomanica
-
native protein, pH 5.5, 25C
5.3
benzaldehyde
B9X0I1, B9X0I2
isoform HNL2, at pH 4.5 and 25C; pH 5.0, 25C
6
benzaldehyde
-
pH 6.0
11.5
benzaldehyde
B7VF77
pH 5.5
38
benzaldehyde
Prunus amygdalus turcomanica
-
enzyme immobilized onto Eupergit C250 L, pH 5.5, 25C
41
benzaldehyde
Prunus amygdalus turcomanica
-
enzyme immobilized onto Eupergit CM, pH 5.5, 25C
3.5
p-anisaldehyde
B7VF77
pH 5.5
2.6
piperonal
B7VF77
pH 5.5
39.3
pivaldehyde
B7VF77
pH 5.5
99.9
propionaldehyde
B7VF77
pH 5.5
41.8
Isobutyraldehyde
B7VF77
pH 5.5
additional information
additional information
-
estimation of kinetic parameters by progress curve analysis
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.03
(R)-Mandelonitrile
E8WYN5
pH 4.5, 25C
56
(R)-Mandelonitrile
B7VF77
pH 5.5
1160
2-naphthaldehyde
B7VF77
pH 5.5
1700
benzaldehyde
B7VF77
pH 5.5
582
p-anisaldehyde
B7VF77
pH 5.5
334
piperonal
B7VF77
pH 5.5
164
pivaldehyde
B7VF77
pH 5.5
223
propionaldehyde
B7VF77
pH 5.5
110
Isobutyraldehyde
B7VF77
pH 5.5
additional information
additional information
-
estimation of kinetic parameters by progress curve analysis
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
348
(R)-Mandelonitrile
B7VF77
pH 5.5
4877
101
2-naphthaldehyde
B7VF77
pH 5.5
2374
148
benzaldehyde
B7VF77
pH 5.5
146
9.6
Isobutyraldehyde
B7VF77
pH 5.5
1646
50.8
p-anisaldehyde
B7VF77
pH 5.5
8164
29.2
piperonal
B7VF77
pH 5.5
13828
14.3
pivaldehyde
B7VF77
pH 5.5
11149
19.4
propionaldehyde
B7VF77
pH 5.5
273
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
1.74
E8WYN5
pH 6.0, 25C
2 - 20
B9X0I1, B9X0I2
pH 5.0, 25C
9
B9X0I1, B9X0I2
(R)-HNL from crude extract, in 0.3 mM citrate buffer, at pH 5.0 and 25C
12.2
-
wild-type, 25C, pH 4.75
23.6
-
surface-modified mutant, 25C, pH 4.5
40.9
B7VF77
-
129
B9X0I1, B9X0I2
isoform HNL2 after purification, in 0.3 mM citrate buffer, at pH 5.0 and 25C; pH 5.0, 25C
133.6
-
wild-type, 25C, pH 6.0
220
B9X0I1, B9X0I2
(R)-HNL after 24.4fold purification, in 0.3 mM citrate buffer, at pH 5.0 and 25C
227
-
surface-modified mutant, 25C, pH 5.75
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
2.5
-
at low pH very low amounts of crude enzyme catalyse stereoselective hydroxypivalaldehyde cyanohydrin formation in water based reaction systems
3.5 - 7
-
because of the base-catalyzed decomposition of mandelonitrile, pH dependence is only determined below pH 7.5. Activity increases from pH 3.5 to 6.2 and levels off between pH 6.2 and 7 for both isoforms
4
-
selected as the assay temperature for the reaction to avoid the non-enzymatic reaction producing racemates of mandelonitrile
4
-
selected as the optimum temperature for the reaction to avoid the non-enzymatic reaction producing racemates of mandelonitrile
4
Prunus amygdalus turcomanica
-
carboligation reaction
4.5
B9X0I1, B9X0I2
;
5 - 6
Prunus sp.
-
-
5
-
assay at
5.5
Prunus amygdalus turcomanica
-
mandelonitrile cleavage reaction, enzyme immobilized onto Eupergit CM and Eupergit C 250 L supports
5.75
-
surface-modified mutant
6
-
optimal pH, but also high non-enzymatic reaction
6
Prunus pseudoarmeniaca
-
optimum pH for free and immobilized enzyme
6
Prunus amygdalus turcomanica
-
mandelonitrile cleavage reaction, native enzyme
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4.5 - 6
B7VF77
pH 4.5: about 40% of maximal activity, pH 6.0: about 30% of maximal activity
4.5
-
surface-modified mutant, less than 10% of maximum activity
4.75
-
wild-type, less than 10% of maximum activity
5
-
almost inactive below
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4
-
effect of buffer pH on the hydrocyanation of acetophenone
5
Prunus amygdalus turcomanica
-
carboligation reaction
10
-
selected as the optimum temperature for the reaction to avoid the non-enzymatic reaction producing racemates of mandelonitrile
10
-
selected as the optimum temperature for the reaction to avoid the non-enzymatic reaction producing racemates of mandelonitrile
15 - 25
-
reaction with benzaldehyde and HCN
25 - 35
B9X0I1, B9X0I2
-
25
-
assay at
25
Prunus pseudoarmeniaca
-
free and immobilized enzyme
25
Prunus amygdalus turcomanica
-
mandelonitrile cleavage reaction
30
-
assay at
35 - 40
-
-
40
-
optimal temperature, but also high non-enzymatic reaction
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
20 - 60
B7VF77
20C: about 50% of maximal activity, 60C: about 40% of maximal activity
50
Prunus pseudoarmeniaca
-
free enzyme retains about 57% of its maximum activity at 50C whereas immobilized enzymes onto Eupergit C and Eupergit C 250 L retain about 75 and 82% of their maximum activities, respectively, at 50C
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5.1
-
isoelectric focusing, wild-type
5.3
-
isoelectric focusing
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
O24243
temporal and spatial expression patterns in flowers and mature seeds. Highest expression levels are detected during floral development. High level of expression in parenchymal cells, both in petals and in the style of the carpe
Manually annotated by BRENDA team
P52706
temporal expression of amygdalin hydrolase and (R)-(+)-mandelonitrile lyase in ripening fruit. Expression may be under transcriptional control during fruit maturation. (R)-(+)-mandelonitrile lyase transcripts are localized within cotyledonary parenchyma cell
Manually annotated by BRENDA team
Prunus pseudoarmeniaca
-
-
Manually annotated by BRENDA team
Prunus amygdalus turcomanica
-
-
Manually annotated by BRENDA team
-
defatted meal
Manually annotated by BRENDA team
O24243
temporal and spatial expression patterns in flowers and mature seeds
Manually annotated by BRENDA team
B9X0I1, B9X0I2
-
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
18000
-
gel filtration
703501
55000 - 80000
Prunus sp.
-
-
650926
57000
B9X0I1, B9X0I2
gel filtration; gel filtration
714536
61000
-
electrospray ionisation mass spectrometry
653932
72000
B7VF77
gel filtration
691375
100000
Prunus amygdalus turcomanica
-
gel filtration
728160
168000
-
isoenzyme A and C, gel filtration
37319
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
G9DE15
x * 14300, SDS-PAGE
?
B9X0I1, B9X0I2
x * 62751, calculated, x * 62000, SDS-PAGE of deglycosylated protein
dimer
-
the enzyme forms dimers in solution
monomer
-
1 * 15000, SDS-PAGE
monomer
Prunus sp.
-
1 * 55000-80000
monomer
B7VF77
1 * 62300, SDS-PAGE
monomer
B9X0I1, B9X0I2
1 * 58100, recombinant (R)-HNL, SDS-PAGE
monomer
B9X0I1, B9X0I2
1 * 62000, non-glycosylated isoform HNL2, SDS-PAGE
monomer
B9X0I1, B9X0I2
1 * 62751, isoform HNL2, calculated from amino acid sequence
monomer
B9X0I1, B9X0I2
1 * 97000, glycosylated isoform HNL2, SDS-PAGE
monomer
B9X0I1, B9X0I2
1 * 58100, SDS-PAGE
multimer
-
x * 20000, SDS-PAGE
tetramer
Prunus amygdalus turcomanica
-
4 * 25000, SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
glycoprotein
B7VF77
-
flavoprotein
B9X0I1, B9X0I2
enzyme shows a typical flavoprotein spectrum with absorption maxima at 389 nm nd 463 nm
glycoprotein
B9X0I1, B9X0I2
molecular mass 97000 Da, mass of deglycosylated protein 62000 Da
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
structure at a crystallographic resolution of 2.5 A and comparison with the S-selective HNL from Hevea brasiliensis. The structures exhibit an alpha/beta-hydrolase fold and a Ser-His-Asp catalytic triad. Modeling of complexes of the enzymes with both (R)- and (S)-mandelonitrile leads to a catalytic mechanism, in which His236 from the catalytic triad acts as a general base and the emerging negative charge on the cyano group is stabilized by main-chain amide groups and an alpha-helix dipole very similar to alpha/beta-hydrolases
-
to 2.5 A resolution, Structure exhibits a cupin fold, and manganese is bound to three histidine and one glutamine residue
E8WYN5
3D structural data of the enzyme with the reaction product benzaldehyde bound within the active site, which allow unambiguous assignment of the location of substrate binding
-
hanging drop vapor diffusion using polyethylene glycol 4000 and isopropanol as coprecipitants. The crystals belong to the monoclinic space group P2(1) with unit cell parameters a = 69.9, b = 95.1, c = 95.6 A, and beta = 118.5 degrees. A complete set of diffraction data collected to 2.6 A resolution on native crystals of isoenzyme III
-
triclinic crystals grown in hanging drops, 1.5 A resolution, space group P1 with cell parameters a = 56.2 A, b = 67.5 A, c = 79.8
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
3 - 9
B7VF77
60 min, stable
691375
4
Prunus pseudoarmeniaca
-
increasing the pH value above 4.0, the yield and ee are dramatically decreased due to the spontaneous chemical decomposition of the product
715946
4.75
-
wild-type, half-life 2.2 min, flavin-based fluorescent reporter fusion protein half-life 55-95 min
726741
5
-
20C, wild-type, half-life 0.16 h, surface-modified mutant, half-life 2.23 h
727311
5.4
-
half-life time: 2 h, the deactivation of the enzyme at slightly acidic pH is a result of pronounced structural unfolding
704762
6
-
20C, wild-type, half-life 60 h, surface-modified mutant, half-life 52.2 h
727311
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0 - 20
-
stable
704762
0
-
pH 5.0, wild-type, half-life 18 min, surface-modified mutant, half-life 137 min
727311
5 - 20
Prunus pseudoarmeniaca
-
free and immobilized enzyme preparations show optimal carboligation activity at 5C. As the temperature is increased from 5 to 20C, the yields decrease, however enantiomeric excess values (99%) unchange
715946
10
-
half-life time: more than 96 h
704762
10
-
pH 5.0, wild-type, half-life 23.6 min, surface-modified mutant, half-life 136 min
727311
20
-
half-life time: 80 h
704762
20
-
pH 5.0, wild-type, half-life 9.6 min, surface-modified mutant, half-life 134 min
727311
25 - 50
Prunus pseudoarmeniaca
-
the half lives of free enzyme at 25 and 50C are 49.9 and 30.5 h, respectively and these correspondingly are 96.3 and 43.6 h for immobilized enzyme onto Eupergit C, and 138.6 and 50.2 h for immobilized enzyme onto Eupergit C 250 L
715946
30
-
half-life time: 33 h
704762
37
-
half-life 6.6 h; half-life time: 6.6 h
704762
50
-
half-life 0.3 h; half-life time: 0.3 h
704762
70
B7VF77
60 min, 68% residual activity
691375
80
B7VF77
60 min, 28% residual activity
691375
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
the enzyme is stabilized by addition of sorbitol and saccharose
-
(R)-oxynitrilase immobilized as a cross-linked enzyme aggregate via precipitation with 1,2-dimethoxyethane and subsequent cross-linking using glutaraldehyde is stable and recyclable
-
both of immobilized enzymes (Eupergit C and Eupergit C250L) are used repeatedly 20times and the residual activities are about 97% of their initial activities
Prunus pseudoarmeniaca
-
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
butyl acetate
-
synthesis of (R)-beta-nitro alcohols, highest enantioselectivity is obtained with n-butyl acetate as solvent with an optimum aqueous phase content of 50% (v/v)
dibutyl ether
-
EjHNL is very stable in ethyl acetate, diethyl ether, methyl-tert-butyl ether, diisopropyl ether, dibutyl ether and hexane for 12 h. The best solvent for the highest initial velocity and enantiomeric excess is diethyl ether with an optimum aqueous phase content of 50% (v/v)
dibutyl ether
-
more than 80% residual activity after incubation for 12 h in the system of methyl-tert-butyl ether, dibutyl ether, hexane, and diisopropyl ether while diethyl ether and ethyl acetate are not suitable solvents
diethyl ether
-
EjHNL is very stable in ethyl acetate, diethyl ether, methyl-tert-butyl ether, diisopropyl ether, dibutyl ether and hexane for 12 h. The best solvent for the highest initial velocity and enantiomeric excess is diethyl ether with an optimum aqueous phase content of 50% (v/v)
diethyl ether
-
more than 80% residual activity after incubation for 12 h in the system of methyl-tert-butyl ether, dibutyl ether, hexane, and diisopropyl ether while diethyl ether and ethyl acetate are not suitable solvents
diisopropyl ether
-
EjHNL is very stable in ethyl acetate, diethyl ether, methyl-tert-butyl ether, diisopropyl ether, dibutyl ether and hexane for 12 h. The best solvent for the highest initial velocity and enantiomeric excess is diethyl ether with an optimum aqueous phase content of 50% (v/v)
diisopropyl ether
-
more than 80% residual activity after incubation for 12 h in the system of methyl-tert-butyl ether, dibutyl ether, hexane, and diisopropyl ether while diethyl ether and ethyl acetate are not suitable solvents
Ethyl acetate
-
EjHNL is very stable in ethyl acetate, diethyl ether, methyl-tert-butyl ether, diisopropyl ether, dibutyl ether and hexane for 12 h. The best solvent for the highest initial velocity and enantiomeric excess is diethyl ether with an optimum aqueous phase content of 50% (v/v)
Ethyl acetate
-
more than 80% residual activity after incubation for 12 h in the system of methyl-tert-butyl ether, dibutyl ether, hexane, and diisopropyl ether while diethyl ether and ethyl acetate are not suitable solvents
hexane
-
EjHNL is very stable in ethyl acetate, diethyl ether, methyl-tert-butyl ether, diisopropyl ether, dibutyl ether and hexane for 12 h. The best solvent for the highest initial velocity and enantiomeric excess is diethyl ether with an optimum aqueous phase content of 50% (v/v)
hexane
-
more than 80% residual activity after incubation for 12 h in the system of methyl-tert-butyl ether, dibutyl ether, hexane, and diisopropyl ether while diethyl ether and ethyl acetate are not suitable solvents
methyl-tert-butylether
-
EjHNL is very stable in ethyl acetate, diethyl ether, methyl-tert-butyl ether, diisopropyl ether, dibutyl ether and hexane for 12 h. The best solvent for the highest initial velocity and enantiomeric excess is diethyl ether with an optimum aqueous phase content of 50% (v/v)
methyl-tert-butylether
-
more than 80% residual activity after incubation for 12 h in the system of methyl-tert-butyl ether, dibutyl ether, hexane, and diisopropyl ether while diethyl ether and ethyl acetate are not suitable solvents
additional information
-
effect of different organic solvents on the hydrocyanation of acetophenone tested
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4C, 20 mM potassium phosphate buffer, pH 6.0, stable for 30 d
B7VF77
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate precipitation and Ni Sepharose column chromatography
-
recombinant enzyme
-
to homogeneity. The final yield, of 36% with 49fold purification, is obtained by 30-80% (NH4)2SO4 fractionation and column chromatography on DEAE-Toyopearl and concanavalin A Sepharose 4B, which suggests the presence of a carbohydrate side chain
B7VF77
-
Prunus amygdalus turcomanica
-
partly, as crosslinked enzyme aggregates. Optimal conditions are initial glutaraldehyde concentration of 25% w/v, ammonium sulfate saturation concentration of 43% w/v, and crosslinking time of 18 h
-
ammonium sulfate precipitation, DEAE Toyopearl column chromatography, phenyl Toyopearl column chromatography, and Superdex 200 gel filtration
B9X0I1, B9X0I2
ammonium sulfate precipitation
Prunus pseudoarmeniaca
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
-
expression in Escherichia coli
-
cloned and sequenced
-
expressed in Pichia pastoris
-
expression of mutant and wild-type enzymes in Pichia pastoris X33
-
overexpressed in Pichia pastoris
-
expresion in Pichia pastoris; expressed in Pichia pastoris strain GS115
B9X0I1, B9X0I2
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
D208N
-
less than 2% residual activity
H236F
-
less than 2% residual activity
M237K
-
no residual activity
N12T
-
less than 2% residual activity
N12T/M237K
-
expression results in insoluble protein
S81A
-
less than 2% residual activity
H459N
-
less than 5% of the activity compared to wild type
H497N
-
less than 5% of the activity compared to wild type
I108M/A111G
-
mutant with improved catalytic properties: recovery of a 89.9% yield of (R)-2-chloromandelonitrile with an enantiomeric excess of 97.6% enantiomeric excess, about 4% residual aldehyde. The mutant also contains two silent mutations at position 85 and position 432
L1Q
-
mutation enhances expression in Pichia pastoris
L1Q/A111G
-
activity is similar to wild-type enzyme with its preferred substrate benzaldehyde. Directed evolution of PaHNL5/L1Q/A11G
M237L
-
100% residual activity
additional information
-
design of a surface-modified variant incorporating 11 changes in the amino acids on the protein surface to stabilze the protein at acidic pH. Mutant shows a broadened pH optimum towards the acidic range, along with enhancement of activity by up to twofold and significantly increased pH- and thermostabilities. The effect is probably due to a shift of the isoelectic point from pH 5.1 to 4.8. Mutant is applicable in aqueous/organic two-phase systems
additional information
-
fusion of enzyme to different fluorescent reporter proteins. All fusion constructs retain enzymatic activity and fluorescence in vivo and in vitro, but show significant differences in activity and pH stability. Flavin-based fluorescent reporter fusions show almost 2 orders of magnitude-increased half-lives in the weakly acidic pH range compared to findings for the wild-type enzyme. This increased stability is apparently caused by oligomerization mediated via the flavin-based tag. The increased stability of the fusion proteins enables the efficient synthesis of (R)-mandelonitrile in an aqueous-organic two-phase system at a pH below 5
L1Q/N3I/I108M/A111G
-
mutant with improved catalytic properties: recovery of a 92.7% yield of (R)-2-chloromandelonitrile with an ee of 98.6% enantiomeric excess, about 2% residual aldehyde, the mutant also contains two silent mutations at position 85 and position 432
additional information
-
directed evolution of PaHNL5/L1Q/A11G (a mutant with activity is similar to wild-type enzyme with its preferred substrate benzaldehyde). 10000 transformants are screened for cleavage or synthesis of (R)-2-chloromandelonitrile
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
-
fusion of enzyme to different fluorescent reporter proteins. Flavin-based fluorescent reporter fusions convert 95% benzaldehyde to (R)-mandelonitrile within 60 min at pH 4.75, with 96% enantiomeric excess
synthesis
-
synthesis of (R)-beta-nitro alcohols using nitromethane as donor. Highest enantioselectivity is obtained with n-butyl acetate as solvent with an optimum aqueous phase content of 50% (v/v)
synthesis
-
optically active cyanoydrins are expedient starting materials for preparation of alpha-hydroxyketones, alpha-hydroxy acids, beta-aminoalcohols, aminonitriles and aziridines
synthesis
-
optically active cyanohydrins are expedient starting materials for preparation of alpha-hydroxyketones, alpha-hydroxy acids, beta-aminoalcohols, aminonitriles and aziridines
synthesis
-
(R)-oxynitrilase immobilized as a cross-linked enzyme aggregate via precipitation with 1,2-dimethoxyethane and subsequent cross-linking using glutaraldehyde is stable and recyclable. Application in microaqueous medium, superior biocatalyst for the enantioselective hydrocyanation of slow-reacting aldehydes
synthesis
-
development and validation of a process model for production of (R)-cyanohydrins in an aqueous-organic biphasic-stirred tank reactor with an unknown interfacial area operated in batch mode. The formation of (R)-mandelonitrile from benzaldehyde and cyanide catalyzed by Prunus amygdalus hydroxynitrile lyase is chosen as a model reaction. Methyl tert-butyl ether is selected as the organic solvent and the reaction conditions are 5C and pH 5.5 at which the nonenzymatic reaction towards rac-mandelonitrile is largely suppressed
synthesis
-
hydroxynitrile lyases are proficient biocatalysts for the stereospecific synthesis of cyanohydrins
synthesis
-
production of (R)-hydroxypivalaldehyde cyanohydrin, the chiral key precursor in hydroxynitrile lyase based (R)-pantlactone synthesis
synthesis
-
the enantiospecific formation of alpha-hydroxynitriles
synthesis
-
purification of enzyme as crosslinked enzyme aggregates and application for synthesis of enantiopure cyanohydrins
synthesis
Prunus sp.
-
used as a catalyst in the preparation of optically active cyanohydrins