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Information on EC 4.1.2.10 - (R)-mandelonitrile lyase
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4.1.2.10 (R)-mandelonitrile lyaseIUBMB Comments
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).
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Word Map
- 4.1.2.10
- cyanohydrin
- prunus
- synthesis
- hcn
- cherry
-
enantioselective
- serotina
- lyases
-
r-mandelonitrile
-
enantiomeric
- amygdalus
-
diisopropyl
- prunasin
-
cyanogenesis
- hbhnl
-
hydrocyanic
-
hevea
-
s-selective
- pharmacology
- agriculture
The enzyme appears in viruses and cellular organisms
Synonyms
mandelonitrile lyase, athnl, (r)-oxynitrilase, (r)-(+)-mandelonitrile lyase, pahnl5, aphnl, r-selective hnl, pahnl1, acix9_0562, (r)-hydroxynitrile lyase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(R)-(+)-Mandelonitrile lyase
(R)-HNL
(R)-hydroxynitrile lyase
(R)-Mandelonitrile lyase
(R)-Oxynitrilase
AciX9_0562
cupin 2 conserved barrel domain protein
D-alpha-hydroxynitrile lyase
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-
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-
D-Hydroxynitrile lyase
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-
-
-
D-Oxynitrilase
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-
-
-
EjHNL
HNL
HNL2
Hydroxynitrile lyase
hydroynitrile lyase
Lyase, mandelonitrile
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-
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MDL
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-
-
-
Oxynitrilase
PaHNL
PaHNL5
PhaMDL
R-selective hydroxynitrile lyase
(R)-(+)-Mandelonitrile lyase
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-
-
-
(R)-Mandelonitrile lyase
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-
-
-
(R)-Oxynitrilase
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-
-
-
Hydroxynitrile lyase
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-
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Oxynitrilase
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-
-
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PhaMDL
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-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(R)-mandelonitrile = cyanide + benzaldehyde
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
(R)-mandelonitrile = cyanide + benzaldehyde
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
cyanohydrin formation
cyanohydrin formation
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-
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PATHWAY SOURCE
PATHWAYS
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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).
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CAS REGISTRY NUMBER
COMMENTARY
9024-43-5
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2-chlorobenzaldehyde + HCN
(R)-2-chloromandelonitrile
-
-
after 96 h, 100% yield, 21% enantiomeric excess
-
?
2-chlorobenzaldehyde + nitromethane
1-(2-chlorophenyl)-2-nitroethanol
-
34% yield after 2 h
-
?
2-heptanone + HCN
(R)-2-heptanone cyanohydrin
-
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
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13% yield after 2 h
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?
2-methylbenzaldehyde + nitromethane
1-(2-methylphenyl)-2-nitroethanol
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12% yield after 2 h
-
?
3,4-dihydroxybenzaldehyde + HCN
(R)-3,4-dihydroxymandelonitrile
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after 96 h, 100% yield, 99% enantiomeric excess
-
?
3-(2-naphthyl)benzaldehyde + nitromethane
(1R)-1-[3-(naphthalen-2-yl)phenyl]-2-nitroethanol
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7% yield after 2 h
-
?
3-chlorobenzaldehyde + nitromethane
1-(3-chlorophenyl)-2-nitroethanol
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17% yield after 2 h
-
?
3-methoxybenzaldehyde + nitromethane
1-(3-methoxyphenyl)-2-nitroethanol
-
17% yield after 2 h
-
?
3-methylbenzaldehyde + nitromethane
1-(3-methylphenyl)-2-nitroethanol
-
12% yield after 2 h
-
?
3-phenylpropionaldehyde + HCN
(R)-2-hydroxy-4-phenylbutyronitrile
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after 96 h, 83% yield, 91% enantiomeric excess
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?
4-bromobenzaldehyde + HCN
(R)-4-bromomandelonitrile
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after 96 h, 100% yield, 99% enantiomeric excess
-
?
4-bromobenzaldehyde + nitromethane
1-(4-bromophenyl)-2-nitroethanol
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20% yield after 2 h
-
?
4-chlorobenzaldehyde + nitromethane
1-(4-chlorophenyl)-2-nitroethanol
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9% yield after 2 h
-
?
4-fluorobenzaldehyde + HCN
(R)-4-fluoromandelonitrile
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after 96 h, 100% yield, 72% enantiomeric excess
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?
4-fluorobenzaldehyde + nitromethane
1-(4-fluorophenyl)-2-nitroethanol
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9% yield after 2 h
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?
4-methoxybenzaldehyde + nitromethane
1-(4-methoxyphenyl)-2-nitroethanol
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2% yield after 2 h
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?
4-methylbenzaldehyde + nitromethane
1-(4-methylphenyl)-2-nitroethanol
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11% yield after 2 h
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?
4-nitrobenzaldehyde + HCN
(R)-4-nitromandelonitrile
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after 96 h, 100% yield, 14% enantiomeric excess
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?
acetyltrimethylsilane + acetone cyanohydrin
?
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both acetyltrimethylsilane conversion and enantiomeric excess of the product are above 99%
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-
?
benzaldehyde + HCN
(R)-mandelonitrile
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after 96 h, 100% yield, 99% enantiomeric excess
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?
benzaldehyde + nitromethane
(R)-2-nitro-1-phenylethanol
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30% yield after 2 h
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?
cyanide + (2E)-3-methylpent-2-enal
(2R,3E)-2-hydroxy-4-methylhex-3-enenitrile
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-
-
-
?
cyanide + (2E)-hex-2-enal
(3E)-2-hydroxyhept-3-enenitrile
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53% enantiomeric excess
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?
cyanide + (2E,4E)-hexa-2,4-dienal
(2R,3E,5E)-2-hydroxyhepta-3,5-dienenitrile
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-
-
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?
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
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-
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
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?
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
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-
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
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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
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?
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
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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
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?
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
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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
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?
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
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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
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-
43.9% (2S)-3-(benzyloxy)-2-hydroxypropanenitrile and 53.1% (2S)-3-(benzyloxy)-2-hydroxypropanenitrile
-
?
cyanide + (R)-4-methylsulfanylbenzaldehyde
(R)-4-methylsulfanyl-mandelonitrile
-
-
-
-
?
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
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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
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?
cyanide + 1-phenylethanone
2-hydroxy-2-phenylpropanenitrile
-
-
-
?
cyanide + 2,2-dimethylpropanal
(2R)-2-hydroxy-3,3-dimethylbutanenitrile
-
activity is 33% of the activity with benzaldehyde
9% enentiomeric excess
-
?
cyanide + 2,3,4a,8a-tetrahydro-1,4-benzodioxine-6-carbaldehyde
(2R)-hydroxy(2,3,4a,8a-tetrahydro-1,4-benzodioxin-6-yl)acetonitrile
-
isoenzyme HNL5
-
-
?
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
-
-
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
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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
-
-
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
-
98% enantiomeric excess
-
?
cyanide + 2-chlorobenzaldehyde
(2R)-2-(2-chlorophenyl)-2-hydroxyacetonitrile
-
-
-
?
cyanide + 2-fluorobenzaldehyde
(2R)-(2-fluorophenyl)(hydroxy)ethanenitrile
-
99% enantiomeric excess
-
?
cyanide + 2-iodobenzaldehyde
(2R)-(2-iodophenyl)(hydroxy)ethanenitrile
-
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
-
-
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-methoxybenzaldehyde
(R)-2-hydroxy-2-(2-methoxyphenyl)acetonitrile
-
-
-
-
?
cyanide + 2-methylbenzaldehyde
(R)-2-hydroxy-2-(2-methylphenyl)acetonitrile
-
-
-
-
?
cyanide + 2-methylpropanal
(2R)-2-hydroxy-3-methylbutanenitrile
-
activity is 67% of the activity with benzaldehyde
13% enentiomeric excess
-
?
cyanide + 2-naphthaldehyde
(R)-2-hydroxy-2-(naphthalen-2-yl)acetonitrile
-
-
-
?
cyanide + 2-phenylpropanal
(2R,3S)-2-hydroxy-3-phenylbutanenitrile + (2S,3R)-2-hydroxy-3-phenylbutanenitrile + (2R,3R)-2-hydroxy-3-phenylbutanenitrile
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-
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
-
-
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-bromobenzaldehyde
(2R)-(3-bromophenyl)(hydroxy)ethanenitrile
-
95% enantiomeric excess
-
?
cyanide + 3-chlorobenzaldehyde
(2R)-(3-chlorophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
cyanide + 3-fluorobenzaldehyde
(2R)-(3-fluorophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
cyanide + 3-hydroxy-2,2-dimethylpropanal
(2R)-2,5-dihydroxy-3,3-dimethylpentanenitrile
-
i.e. hydroxypivaldehyde
best enantiomeric excess is obtained at pH 2.5
-
?
cyanide + 3-iodobenzaldehyde
(2R)-(3-iodophenyl)(hydroxy)ethanenitrile
-
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
-
-
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-methoxybenzaldehyde
(2R)-(3-methoxyphenyl)(hydroxy)ethanenitrile
-
-
-
?
cyanide + 3-methylbenzaldehyde
(2R)-(3-methylphenyl)(hydroxy)ethanenitrile
-
-
-
?
cyanide + 3-phenoxybenzaldehyde
(2R)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
-
more than 95% enantiomeric excess
-
?
cyanide + 3-phenoxybenzaldehyde
(R)-2-hydroxy-2-(3-phenoxy-phenyl)-acetonitrile
-
synthesis of (R)-2-hydroxy-2-(3-phenoxyphenyl)-acetonitrile with 93% enantiomeric excess
-
-
?
cyanide + 3-phenoxypropanal
(2R)-2-hydroxy-5-phenylpentanenitrile
-
-
74.3% (2R)-2-hydroxy-5-phenylpentanenitrile and 25.7% (2S)-2-hydroxy-5-phenylpentanenitrile
-
?
cyanide + 3-phenylprop-2-enal
(2R)-2-hydroxy-4-phenylbut-3-enenitrile
-
-
-
?
cyanide + 3-phenylpropanal
(R)-2-hydroxy-4-phenylbutyronitrile
-
isoenzyme HNL5
-
-
?
cyanide + 3-tetrahydrothiophenone
(S)-3-hydroxytetrahydrothiophene-3-carbonitrile
-
the enzyme, that shows (R)-stereospecificity for its natural substrate shows S-stereselectivity with the heterocyclic ketone as substrate
-
-
?
cyanide + 4-bromoacetophenone
4-bromo-2-hydroxyphenylpropionitrile
-
(R)-cyanohydrin is formed with 5% yield and 99% enantiomeric excess, after 96 h at pH 4.0 and 5°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
-
-
r
cyanide + 4-bromobenzaldehyde
(R)-4-bromomandelonitrile
-
synthesis of (R)-4-bromomandelonitrile with a yield pf 100% and an enantiomeric excess value of 99%
-
-
?
cyanide + 4-chloroacetophenone
4-chloro-2-hydroxyphenylpropionitrile
-
(R)-cyanohydrin is formed with 11% yield and 95% enantiomeric excess, after 96 h at pH 4.0 and 5°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
-
-
r
cyanide + 4-chlorobenzaldehyde
(2R)-(4-chlorophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
cyanide + 4-fluoroacetophenone
4-fluoro-2-hydroxyphenylpropionitrile
-
(R)-cyanohydrin is formed with 20% yield and 84% enantiomeric excess, after 96 h at pH 4.0 and 5°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
-
-
r
cyanide + 4-fluorobenzaldehyde
(2R)-(4-fluorophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
cyanide + 4-hydroxybenzaldehyde
(2R)-(4-hydroxyphenyl)(hydroxy)ethanenitrile
-
97% enantiomeric excess
-
?
cyanide + 4-hydroxybutanal
(R)-2,5-dihydroxypentanenitrile
-
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 15°C
-
-
?
cyanide + 4-iodoacetophenone
4-iodo-2-hydroxyphenylpropionitrile
-
(R)-cyanohydrin is formed with 3% yield and 24% enantiomeric excess, after 96 h at pH 4.0 and 5°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
-
-
r
cyanide + 4-iodobenzaldehyde
(2R)-(4-iodophenyl)(hydroxy)ethanenitrile
-
92% enantiomeric excess
-
?
cyanide + 4-methyl benzaldehyde
(2R)-(4-methylphenyl)(hydroxy)ethanenitrile
-
(R)-cyanohydrin is formed with 85% yield and 79% enantiomeric excess, after 96 h at pH 4.0 and 5°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
-
-
r
cyanide + 4-nitrobenzaldehyde
(R)-4-nitromandelonitrile
-
synthesis of (R)-4-nitromandelonitrile with a yield of 100% and an enantiomeric excess value of 14%
-
-
?
cyanide + 4-phenylbutanal
(2R)-2-hydroxy-5-phenylpentanenitrile
-
-
88.9% (2R)-2-hydroxy-5-phenylpentanenitrile and 11.1% (2S)-2-hydroxy-5-phenylpentanenitrile
-
?
cyanide + 5-hydroxypentanal
(R)-2,6-dihydroxyhexanenitrile
-
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 15°C
-
-
?
cyanide + 6-methylhept-5-en-2-one
(2R)-2-hydroxy-2,6-dimethylhept-5-enenitrile
-
-
-
?
cyanide + acetophenone
(2R)-hydroxyphenylpropionitrile
-
(R)-cyanohydrin is formed with 1% yield and 99% enantiomeric excess, after 96 h at pH 4.0 and 5°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
-
-
r
cyanide + cinnamaldehyde
(2R,3E)-2-hydroxy-4-phenylbut-3-enenitrile
-
i.e. (2E)-3-phenylprop-2-enal
-
-
?
cyanide + cyclohexanecarbaldehyde
(2R)-cyclohexyl(hydroxy)acetonitrile
-
activity is 41% of the activity with benzaldehyde
10% enentiomeric excess
-
?
cyanide + decanal
(2R)-2-hydroxyundecanal
-
56% enantiomeric excess
-
?
cyanide + furan-2-carbaldehyde
(2R)-(furan-2-yl)(hydroxy)acetonitrile
-
isoenzyme HNL5
-
-
?
cyanide + furan-2-carbaldehyde
(2S)-furan-2-yl-hydroxyacetonitrile
-
-
-
?
cyanide + hexanal
(2R)-2-hydroxyheptanenitrile
-
98% enantiomeric excess
-
?
cyanide + hydroxypivaldehyde
(R)-hydroxypivaldehyde cyanohydrin
-
crosslinked enzyme aggregates catalyze synthesis of (R)-hydroxypivaldehyde cyanohydrin under reaction conditions that immediately inactivated non-immobilized enzyme
-
-
r
cyanide + naphthalen-2-ylacetaldehyde
(2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
-
-
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
-
-
33.2% (2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile and 66.8% (2S)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
-
?
cyanide + naphthalene-1-carbaldehyde
(2R)-hydroxy(naphthalen-1-yl)acetonitrile
-
isoenzyme HNL5
-
-
?
cyanide + naphthalene-2-carbaldehyde
(2R)-hydroxy(naphthalen-2-yl)acetonitrile
-
isoenzyme HNL5
-
-
?
cyanide + naphthalene-2-carbaldehyde
(2R)-hydroxy(naphthalen-2-yl)ethanenitrile
-
-
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
-
-
-
?
cyanide + piperonal
(R)-2-hydroxy-2-(3,4-methylenedioxyphenyl)acetonitrile
-
-
-
?
cyanide + propanal
(2R)-2-hydroxybutanenitrile
-
activity is 20% of the activity with benzaldehyde
7% enentiomeric excess
-
?
cyanide + pyridine-3-carbaldehyde
(2R)-hydroxy(pyridin-3-yl)acetonitrile
-
isoenzyme HNL5
-
-
?
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
-
-
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
-
-
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)acetonitrile
-
isoenzyme HNL5
-
-
?
cyanide + thiophene-2-carbaldehyde
(2S)-hydroxy(thiophen-2-yl)ethanenitrile
-
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
-
separation of enantiomers not posible
-
?
HCN + 1-naphthalenecarboxaldehyde
(R)-2-hydroxy-2-(1-naphthyl)acetonitrile
-
60% conversion
93% enantiomeric excess
-
?
HCN + 2,3,4,5-tetrafluorobenzaldehyde
(R)-2-hydroxy-2-(2,3,4,5-tetrafluorophenyl)acetonitrile
-
26% conversion
23% enantiomeric excess
-
?
HCN + 2,3,4-trimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3,4-trimethoxyphenyl)acetonitrile
-
14% conversion
% enantiomeric excess
-
?
HCN + 2,3,5,6-tetrafluorobenzaldehyde
(R)-2-hydroxy-2-(2,3,5,6-tetrafluorophenyl)acetonitrile
-
21% conversion
12% enantiomeric excess
-
?
HCN + 2,3,5-trimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3,5-trimethoxyphenyl)acetonitrile
-
16% conversion
28% enantiomeric excess
-
?
HCN + 2,3-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,3-dichlorophenyl)acetonitrile
-
11% conversion
22% enantiomeric excess
-
?
HCN + 2,3-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3-dimethoxyphenyl)acetonitrile
-
7% conversion
37% enantiomeric excess
-
?
HCN + 2,4-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,4-dichlorophenyl)acetonitrile
-
13% conversion
78% enantiomeric excess
-
?
HCN + 2,4-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,4-dimethoxyphenyl)acetonitrile
-
11% conversion
48% enantiomeric excess
-
?
HCN + 2,4-dimethylbenzaldehyde
(R)-2-hydroxy-2-(2,4-dimethylphenyl)acetonitrile
-
5.8% conversion
86% enantiomeric excess
-
?
HCN + 2,5-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,5-dichlorophenyl)acetonitrile
-
8.8% conversion
57% enantiomeric excess
-
?
HCN + 2,5-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,5-dimethoxyphenyl)acetonitrile
-
9% conversion
63% enantiomeric excess
-
?
HCN + 2,6-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,6-dichlorophenyl)acetonitrile
-
10% conversion
12% enantiomeric excess
-
?
HCN + 2,6-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,6-dimethoxyphenyl)acetonitrile
-
6.5% conversion
32% enantiomeric excess
-
?
HCN + 2-allylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-allylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-allylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-allylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-allyloxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-allyloxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-allyloxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-allyloxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-butanone
(R)-2-hydroxy-2-methylbutyronitrile
-
48% conversion
72% enantiomeric excess
-
?
HCN + 2-decanone
(R)-2-hydroxy-2-methyl-decanenitrile
-
18% conversion
52% enantiomeric excess
-
?
HCN + 2-ethoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-ethoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-ethoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-ethoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-ethylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-ethylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-ethylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-methylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-furancarboxaldehyde
(S)-2-hydroxy-2-(2-furyl)acetonitrile
-
1.2% conversion
98% enantiomeric excess
-
?
HCN + 2-heptanone
(R)-2-hydroxy-2-methyl-heptanenitrile
-
39% conversion
74% enantiomeric excess
-
?
HCN + 2-hexanone
(R)-2-hydroxy-2-methyl-hexanenitrile
-
48% conversion
80% enantiomeric excess
-
?
HCN + 2-methoxybenzaldehyde
(R)-2-hydroxy-2-(2-methoxyphenyl)acetonitrile
-
6.0% conversion
41% enantiomeric excess
-
?
HCN + 2-methoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-methoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-methoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-methoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-methylbenzaldehyde
(R)-2-hydroxy-2-(2-methylphenyl)acetonitrile
-
6% conversion
61% enantiomeric excess
-
?
HCN + 2-methylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-methylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-methylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-methylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-n-propoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-n-propoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-n-propoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-n-propoxycyclohexanecarbonitrile
-
-
-
-