Any feedback?
No. of entries
Information on EC 4.1.2.10 - (R)-mandelonitrile lyase
for references in articles please use BRENDA:EC4.1.2.10
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
IUBMB 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).
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
- 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
showSynonyms
mandelonitrile lyase, athnl, (r)-oxynitrilase, pahnl5, (r)-(+)-mandelonitrile lyase, r-selective hnl, pahnl1, aphnl, pmhnl, ejhnl, more
topPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
-
-
-
-
D-Hydroxynitrile lyase
-
-
-
-
D-Oxynitrilase
-
-
-
-
EjHNL
HNL
HNL2
Hydroxynitrile lyase
hydroynitrile lyase
Lyase, mandelonitrile
-
-
-
-
MDL
-
-
-
-
Oxynitrilase
PaHNL
PaHNL5
PhaMDL
R-selective hydroxynitrile lyase
(R)-(+)-Mandelonitrile lyase
-
-
-
-
(R)-Mandelonitrile lyase
-
-
-
-
(R)-Oxynitrilase
-
-
-
-
Hydroxynitrile lyase
-
-
-
-
Oxynitrilase
-
-
-
-
PhaMDL
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
cyanohydrin formation
cyanohydrin formation
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PATHWAY SOURCE
PATHWAYS
MetaCyc
amygdalin and prunasin degradation, vicianin bioactivation
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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).
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CAS REGISTRY NUMBER
COMMENTARY
9024-43-5
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R)-4-hydroxymandelonitrile
cyanide + 4-hydroxybenzaldehyde
-
Substrates: -
Products: -
Products: -
r
2-chlorobenzaldehyde + HCN
(R)-2-chloromandelonitrile
-
Substrates: -
Products: after 96 h, 100% yield, 21% enantiomeric excess
Products: after 96 h, 100% yield, 21% enantiomeric excess
?
2-chlorobenzaldehyde + nitromethane
1-(2-chlorophenyl)-2-nitroethanol
Substrates: -
Products: 34% yield after 2 h
Products: 34% yield after 2 h
?
2-heptanone + HCN
(R)-2-heptanone cyanohydrin
-
Substrates: 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
Products: -
Products: -
?
2-methoxybenzaldehyde + nitromethane
1-(2-methoxyphenyl)-2-nitroethanol
Substrates: -
Products: 13% yield after 2 h
Products: 13% yield after 2 h
?
2-methylbenzaldehyde + nitromethane
1-(2-methylphenyl)-2-nitroethanol
Substrates: -
Products: 12% yield after 2 h
Products: 12% yield after 2 h
?
3,4-dihydroxybenzaldehyde + HCN
(R)-3,4-dihydroxymandelonitrile
-
Substrates: -
Products: after 96 h, 100% yield, 99% enantiomeric excess
Products: after 96 h, 100% yield, 99% enantiomeric excess
?
3-(2-naphthyl)benzaldehyde + nitromethane
(1R)-1-[3-(naphthalen-2-yl)phenyl]-2-nitroethanol
Substrates: -
Products: 7% yield after 2 h
Products: 7% yield after 2 h
?
3-chlorobenzaldehyde + nitromethane
1-(3-chlorophenyl)-2-nitroethanol
Substrates: -
Products: 17% yield after 2 h
Products: 17% yield after 2 h
?
3-methoxybenzaldehyde + nitromethane
1-(3-methoxyphenyl)-2-nitroethanol
Substrates: -
Products: 17% yield after 2 h
Products: 17% yield after 2 h
?
3-methylbenzaldehyde + nitromethane
1-(3-methylphenyl)-2-nitroethanol
Substrates: -
Products: 12% yield after 2 h
Products: 12% yield after 2 h
?
3-phenylpropionaldehyde + HCN
(R)-2-hydroxy-4-phenylbutyronitrile
-
Substrates: -
Products: after 96 h, 83% yield, 91% enantiomeric excess
Products: after 96 h, 83% yield, 91% enantiomeric excess
?
4-bromobenzaldehyde + HCN
(R)-4-bromomandelonitrile
-
Substrates: -
Products: after 96 h, 100% yield, 99% enantiomeric excess
Products: after 96 h, 100% yield, 99% enantiomeric excess
?
4-bromobenzaldehyde + nitromethane
1-(4-bromophenyl)-2-nitroethanol
Substrates: -
Products: 20% yield after 2 h
Products: 20% yield after 2 h
?
4-chlorobenzaldehyde + nitromethane
1-(4-chlorophenyl)-2-nitroethanol
Substrates: -
Products: 9% yield after 2 h
Products: 9% yield after 2 h
?
4-fluorobenzaldehyde + HCN
(R)-4-fluoromandelonitrile
-
Substrates: -
Products: after 96 h, 100% yield, 72% enantiomeric excess
Products: after 96 h, 100% yield, 72% enantiomeric excess
?
4-fluorobenzaldehyde + nitromethane
1-(4-fluorophenyl)-2-nitroethanol
Substrates: -
Products: 9% yield after 2 h
Products: 9% yield after 2 h
?
4-methoxybenzaldehyde + nitromethane
1-(4-methoxyphenyl)-2-nitroethanol
Substrates: -
Products: 2% yield after 2 h
Products: 2% yield after 2 h
?
4-methylbenzaldehyde + nitromethane
1-(4-methylphenyl)-2-nitroethanol
Substrates: -
Products: 11% yield after 2 h
Products: 11% yield after 2 h
?
4-nitrobenzaldehyde + HCN
(R)-4-nitromandelonitrile
-
Substrates: -
Products: after 96 h, 100% yield, 14% enantiomeric excess
Products: after 96 h, 100% yield, 14% enantiomeric excess
?
acetyltrimethylsilane + acetone cyanohydrin
?
-
Substrates: both acetyltrimethylsilane conversion and enantiomeric excess of the product are above 99%
Products: -
Products: -
?
benzaldehyde + HCN
(R)-mandelonitrile
-
Substrates: -
Products: after 96 h, 100% yield, 99% enantiomeric excess
Products: after 96 h, 100% yield, 99% enantiomeric excess
?
benzaldehyde + nitromethane
(R)-2-nitro-1-phenylethanol
Substrates: -
Products: 30% yield after 2 h
Products: 30% yield after 2 h
?
cyanide + (2E)-3-methylpent-2-enal
(2R,3E)-2-hydroxy-4-methylhex-3-enenitrile
-
Substrates: -
Products: -
Products: -
?
cyanide + (2E)-hex-2-enal
(2R,3E)-2-hydroxyhept-3-enenitrile
-
Substrates: -
Products: -
Products: -
?
cyanide + (2E)-hex-2-enal
(3E)-2-hydroxyhept-3-enenitrile
Substrates: -
Products: 53% enantiomeric excess
Products: 53% enantiomeric excess
?
cyanide + (2E,4E)-hexa-2,4-dienal
(2R,3E,5E)-2-hydroxyhepta-3,5-dienenitrile
-
Substrates: -
Products: -
Products: -
?
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
-
Substrates: -
Products: 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
Products: 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
-
Substrates: -
Products: 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
Products: 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
-
Substrates: -
Products: 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
Products: 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
-
Substrates: -
Products: 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
Products: 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
-
Substrates: -
Products: 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
Products: 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
-
Substrates: -
Products: 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
Products: 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
-
Substrates: -
Products: 43.9% (2S)-3-(benzyloxy)-2-hydroxypropanenitrile and 53.1% (2S)-3-(benzyloxy)-2-hydroxypropanenitrile
Products: 43.9% (2S)-3-(benzyloxy)-2-hydroxypropanenitrile and 53.1% (2S)-3-(benzyloxy)-2-hydroxypropanenitrile
?
cyanide + (R)-4-methylsulfanylbenzaldehyde
(R)-4-methylsulfanyl-mandelonitrile
-
Substrates: -
Products: -
Products: -
?
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
-
Substrates: -
Products: 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
Products: 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
2-hydroxy-2-phenylpropanenitrile
Substrates: -
Products: -
Products: -
?
cyanide + 2,2-dimethylpropanal
(2R)-2-hydroxy-3,3-dimethylbutanenitrile
-
Substrates: activity is 33% of the activity with benzaldehyde
Products: 9% enentiomeric excess
Products: 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
-
Substrates: isoenzyme HNL5
Products: -
Products: -
?
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
-
Substrates: -
Products: 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
Products: 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
-
Substrates: -
Products: 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
Products: 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
-
Substrates: -
Products: 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
Products: 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
Substrates: -
Products: 98% enantiomeric excess
Products: 98% enantiomeric excess
?
cyanide + 2-chlorobenzaldehyde
(2R)-2-(2-chlorophenyl)-2-hydroxyacetonitrile
Substrates: -
Products: -
Products: -
?
cyanide + 2-fluorobenzaldehyde
(2R)-(2-fluorophenyl)(hydroxy)ethanenitrile
Substrates: -
Products: 99% enantiomeric excess
Products: 99% enantiomeric excess
?
cyanide + 2-iodobenzaldehyde
(2R)-(2-iodophenyl)(hydroxy)ethanenitrile
Substrates: -
Products: more than 95% enantiomeric excess
Products: 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
-
Substrates: -
Products: 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
Products: 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
-
Substrates: -
Products: -
Products: -
?
cyanide + 2-methoxybenzaldehyde
(R)-2-methoxymandelonitrile
-
Substrates: -
Products: -
Products: -
r
cyanide + 2-methylbenzaldehyde
(R)-2-hydroxy-2-(2-methylphenyl)acetonitrile
-
Substrates: -
Products: -
Products: -
?
cyanide + 2-methylpropanal
(2R)-2-hydroxy-3-methylbutanenitrile
-
Substrates: activity is 67% of the activity with benzaldehyde
Products: 13% enentiomeric excess
Products: 13% enentiomeric excess
?
cyanide + 2-naphthaldehyde
(R)-2-hydroxy-2-(naphthalen-2-yl)acetonitrile
Substrates: -
Products: -
Products: -
?
cyanide + 2-phenylpropanal
(2R,3S)-2-hydroxy-3-phenylbutanenitrile + (2S,3R)-2-hydroxy-3-phenylbutanenitrile + (2R,3R)-2-hydroxy-3-phenylbutanenitrile
-
Substrates: -
Products: 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
Products: 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 + 2-thiophenecarboxaldehyde
?
Substrates: -
Products: -
Products: -
?
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
-
Substrates: -
Products: 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
Products: 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
Substrates: -
Products: 95% enantiomeric excess
Products: 95% enantiomeric excess
?
cyanide + 3-chlorobenzaldehyde
(2R)-(3-chlorophenyl)(hydroxy)ethanenitrile
Substrates: -
Products: more than 99% enantiomeric excess
Products: more than 99% enantiomeric excess
?
cyanide + 3-chlorobenzaldehyde
(R)-3-chloromandelonitrile
-
Substrates: -
Products: -
Products: -
r
cyanide + 3-fluorobenzaldehyde
(2R)-(3-fluorophenyl)(hydroxy)ethanenitrile
Substrates: -
Products: more than 99% enantiomeric excess
Products: more than 99% enantiomeric excess
?
cyanide + 3-hydroxy-2,2-dimethylpropanal
(2R)-2,5-dihydroxy-3,3-dimethylpentanenitrile
-
Substrates: i.e. hydroxypivaldehyde
Products: best enantiomeric excess is obtained at pH 2.5
Products: best enantiomeric excess is obtained at pH 2.5
?
cyanide + 3-iodobenzaldehyde
(2R)-(3-iodophenyl)(hydroxy)ethanenitrile
Substrates: -
Products: 93% enantiomeric excess
Products: 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
-
Substrates: -
Products: 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
Products: 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
Substrates: -
Products: -
Products: -
?
cyanide + 3-methoxybenzaldehyde
(R)-3-methoxymandelonitrile
-
Substrates: -
Products: -
Products: -
r
cyanide + 3-methylbenzaldehyde
(2R)-(3-methylphenyl)(hydroxy)ethanenitrile
Substrates: -
Products: -
Products: -
?
cyanide + 3-phenoxybenzaldehyde
(2R)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
Substrates: -
Products: more than 95% enantiomeric excess
Products: more than 95% enantiomeric excess
?
cyanide + 3-phenoxybenzaldehyde
(R)-2-hydroxy-2-(3-phenoxy-phenyl)-acetonitrile
-
Substrates: synthesis of (R)-2-hydroxy-2-(3-phenoxyphenyl)-acetonitrile with 93% enantiomeric excess
Products: -
Products: -
?
cyanide + 3-phenoxybenzaldehyde
(R)-3-phenoxymandelonitrile
-
Substrates: -
Products: -
Products: -
r
cyanide + 3-phenoxypropanal
(2R)-2-hydroxy-5-phenylpentanenitrile
-
Substrates: -
Products: 74.3% (2R)-2-hydroxy-5-phenylpentanenitrile and 25.7% (2S)-2-hydroxy-5-phenylpentanenitrile
Products: 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
Substrates: -
Products: -
Products: -
?
cyanide + 3-phenylpropanal
(R)-2-hydroxy-4-phenylbutyronitrile
-
Substrates: isoenzyme HNL5
Products: -
Products: -
?
cyanide + 3-tetrahydrothiophenone
(S)-3-hydroxytetrahydrothiophene-3-carbonitrile
-
Substrates: the enzyme, that shows (R)-stereospecificity for its natural substrate shows S-stereselectivity with the heterocyclic ketone as substrate
Products: -
Products: -
?
cyanide + 4-biphenylcarboxaldehyde
?
Substrates: -
Products: -
Products: -
?
cyanide + 4-bromoacetophenone
4-bromo-2-hydroxyphenylpropionitrile
-
Substrates: (R)-cyanohydrin is formed with 5% yield and 99% enantiomeric excess, after 96 h at pH 4.0 and 5Ā°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
Products: -
Products: -
r
cyanide + 4-bromobenzaldehyde
(R)-4-bromomandelonitrile
-
Substrates: synthesis of (R)-4-bromomandelonitrile with a yield pf 100% and an enantiomeric excess value of 99%
Products: -
Products: -
?
cyanide + 4-chloroacetophenone
4-chloro-2-hydroxyphenylpropionitrile
-
Substrates: (R)-cyanohydrin is formed with 11% yield and 95% enantiomeric excess, after 96 h at pH 4.0 and 5Ā°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
Products: -
Products: -
r
cyanide + 4-chlorobenzaldehyde
(2R)-(4-chlorophenyl)(hydroxy)ethanenitrile
Substrates: -
Products: more than 99% enantiomeric excess
Products: more than 99% enantiomeric excess
?
cyanide + 4-fluoroacetophenone
4-fluoro-2-hydroxyphenylpropionitrile
-
Substrates: (R)-cyanohydrin is formed with 20% yield and 84% enantiomeric excess, after 96 h at pH 4.0 and 5Ā°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
Products: -
Products: -
r
cyanide + 4-fluorobenzaldehyde
(2R)-(4-fluorophenyl)(hydroxy)ethanenitrile
Substrates: -
Products: more than 99% enantiomeric excess
Products: more than 99% enantiomeric excess
?
cyanide + 4-hydroxybenzaldehyde
(2R)-(4-hydroxyphenyl)(hydroxy)ethanenitrile
Substrates: -
Products: 97% enantiomeric excess
Products: 97% enantiomeric excess
?
cyanide + 4-hydroxybutanal
(R)-2,5-dihydroxypentanenitrile
-
Substrates: 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 15Ā°C
Products: -
Products: -
?
cyanide + 4-iodoacetophenone
4-iodo-2-hydroxyphenylpropionitrile
-
Substrates: (R)-cyanohydrin is formed with 3% yield and 24% enantiomeric excess, after 96 h at pH 4.0 and 5Ā°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
Products: -
Products: -
r
cyanide + 4-iodobenzaldehyde
(2R)-(4-iodophenyl)(hydroxy)ethanenitrile
Substrates: -
Products: 92% enantiomeric excess
Products: 92% enantiomeric excess
?
cyanide + 4-methoxybenzaldehyde
(R)-4-methoxymandelonitrile
-
Substrates: -
Products: -
Products: -
r
cyanide + 4-methyl benzaldehyde
(2R)-(4-methylphenyl)(hydroxy)ethanenitrile
-
Substrates: (R)-cyanohydrin is formed with 85% yield and 79% enantiomeric excess, after 96 h at pH 4.0 and 5Ā°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
Products: -
Products: -
r
cyanide + 4-methylbenzaldehyde
(R)-4-methylmandelonitrile
-
Substrates: -
Products: -
Products: -
r
cyanide + 4-nitrobenzaldehyde
(R)-4-nitromandelonitrile
-
Substrates: synthesis of (R)-4-nitromandelonitrile with a yield of 100% and an enantiomeric excess value of 14%
Products: -
Products: -
?
cyanide + 4-phenylbutan-2-one
2-hydroxy-4-phenylbutyronitrile
-
Substrates: -
Products: -
Products: -
?
cyanide + 4-phenylbutanal
(2R)-2-hydroxy-5-phenylpentanenitrile
-
Substrates: -
Products: 88.9% (2R)-2-hydroxy-5-phenylpentanenitrile and 11.1% (2S)-2-hydroxy-5-phenylpentanenitrile
Products: 88.9% (2R)-2-hydroxy-5-phenylpentanenitrile and 11.1% (2S)-2-hydroxy-5-phenylpentanenitrile
?
cyanide + 5-hydroxypentanal
(R)-2,6-dihydroxyhexanenitrile
-
Substrates: 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 15Ā°C
Products: -
Products: -
?
cyanide + 6-methylhept-5-en-2-one
(2R)-2-hydroxy-2,6-dimethylhept-5-enenitrile
Substrates: -
Products: -
Products: -
?
cyanide + acetophenone
(2R)-hydroxyphenylpropionitrile
-
Substrates: (R)-cyanohydrin is formed with 1% yield and 99% enantiomeric excess, after 96 h at pH 4.0 and 5Ā°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
Products: -
Products: -
r
cyanide + cinnamaldehyde
(2R,3E)-2-hydroxy-4-phenylbut-3-enenitrile
-
Substrates: i.e. (2E)-3-phenylprop-2-enal
Products: -
Products: -
?
cyanide + cyclohexanecarbaldehyde
(2R)-cyclohexyl(hydroxy)acetonitrile
-
Substrates: activity is 41% of the activity with benzaldehyde
Products: 10% enentiomeric excess
Products: 10% enentiomeric excess
?
cyanide + cyclohexanone
1-hydroxycyclohexanecarbonitrile
Substrates: -
Products: -
Products: -
?
cyanide + decanal
(2R)-2-hydroxyundecanal
Substrates: -
Products: 56% enantiomeric excess
Products: 56% enantiomeric excess
?
cyanide + furan-2-carbaldehyde
(2R)-(furan-2-yl)(hydroxy)acetonitrile
-
Substrates: isoenzyme HNL5
Products: -
Products: -
?
cyanide + furan-2-carbaldehyde
(2S)-furan-2-yl-hydroxyacetonitrile
Substrates: -
Products: -
Products: -
?
cyanide + hexanal
(2R)-2-hydroxyheptanenitrile
Substrates: -
Products: 98% enantiomeric excess
Products: 98% enantiomeric excess
?
cyanide + hydroxypivaldehyde
(R)-hydroxypivaldehyde cyanohydrin
-
Substrates: crosslinked enzyme aggregates catalyze synthesis of (R)-hydroxypivaldehyde cyanohydrin under reaction conditions that immediately inactivated non-immobilized enzyme
Products: -
Products: -
r
cyanide + isobutyraldehyde
2-hydroxy-3-methylbutyronitrile
Substrates: -
Products: -
Products: -
?
cyanide + naphthalen-2-ylacetaldehyde
(2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
-
Substrates: -
Products: 3.5% (2S)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile and 96.5% (2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
Products: 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
-
Substrates: -
Products: 33.2% (2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile and 66.8% (2S)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
Products: 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
-
Substrates: isoenzyme HNL5
Products: -
Products: -
?
cyanide + naphthalene-2-carbaldehyde
(2R)-hydroxy(naphthalen-2-yl)acetonitrile
-
Substrates: isoenzyme HNL5
Products: -
Products: -
?
cyanide + naphthalene-2-carbaldehyde
(2R)-hydroxy(naphthalen-2-yl)ethanenitrile
-
Substrates: -
Products: 97.6% (2R)-hydroxy(naphthalen-2-yl)ethanenitrile and 2.4% (2S)-hydroxy(naphthalen-2-yl)ethanenitrile
Products: 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
Substrates: -
Products: -
Products: -
?
cyanide + piperonal
(R)-2-hydroxy-2-(3,4-methylenedioxyphenyl)acetonitrile
Substrates: -
Products: -
Products: -
?
cyanide + propanal
(2R)-2-hydroxybutanenitrile
-
Substrates: activity is 20% of the activity with benzaldehyde
Products: 7% enentiomeric excess
Products: 7% enentiomeric excess
?
cyanide + propionaldehyde
2-hydroxybutyronitrile
Substrates: -
Products: -
Products: -
?
cyanide + pyridine-3-carbaldehyde
(2R)-hydroxy(pyridin-3-yl)acetonitrile
-
Substrates: isoenzyme HNL5
Products: -
Products: -
?
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
-
Substrates: -
Products: 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
Products: 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
-
Substrates: -
Products: 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
Products: 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
-
Substrates: isoenzyme HNL5
Products: -
Products: -
?
cyanide + thiophene-2-carbaldehyde
(2S)-hydroxy(thiophen-2-yl)ethanenitrile
-
Substrates: activity is 2fold higher than with benzaldehyde
Products: 75% enentiomeric excess, The (S)-configuration is due to the Cahn-Ingold-Prelog rules
Products: 75% enentiomeric excess, The (S)-configuration is due to the Cahn-Ingold-Prelog rules
?
cyanide + thiophene-2-carbaldehyde
hydroxy(thiophen-2-yl)ethanenitrile
Substrates: -
Products: separation of enantiomers not posible
Products: separation of enantiomers not posible
?
HCN + 1-naphthalenecarboxaldehyde
(R)-2-hydroxy-2-(1-naphthyl)acetonitrile
-
Substrates: 60% conversion
Products: 93% enantiomeric excess
Products: 93% enantiomeric excess
?
HCN + 2,3,4,5-tetrafluorobenzaldehyde
(R)-2-hydroxy-2-(2,3,4,5-tetrafluorophenyl)acetonitrile
-
Substrates: 26% conversion
Products: 23% enantiomeric excess
Products: 23% enantiomeric excess
?
HCN + 2,3,4-trimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3,4-trimethoxyphenyl)acetonitrile
-
Substrates: 14% conversion
Products: % enantiomeric excess
Products: % enantiomeric excess
?
HCN + 2,3,5,6-tetrafluorobenzaldehyde
(R)-2-hydroxy-2-(2,3,5,6-tetrafluorophenyl)acetonitrile
-
Substrates: 21% conversion
Products: 12% enantiomeric excess
Products: 12% enantiomeric excess
?
HCN + 2,3,5-trimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3,5-trimethoxyphenyl)acetonitrile
-
Substrates: 16% conversion
Products: 28% enantiomeric excess
Products: 28% enantiomeric excess
?
HCN + 2,3-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,3-dichlorophenyl)acetonitrile
-
Substrates: 11% conversion
Products: 22% enantiomeric excess
Products: 22% enantiomeric excess
?
HCN + 2,3-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3-dimethoxyphenyl)acetonitrile
-
Substrates: 7% conversion
Products: 37% enantiomeric excess
Products: 37% enantiomeric excess
?
HCN + 2,4-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,4-dichlorophenyl)acetonitrile
-
Substrates: 13% conversion
Products: 78% enantiomeric excess
Products: 78% enantiomeric excess
?
HCN + 2,4-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,4-dimethoxyphenyl)acetonitrile
-
Substrates: 11% conversion
Products: 48% enantiomeric excess
Products: 48% enantiomeric excess
?
HCN + 2,4-dimethylbenzaldehyde
(R)-2-hydroxy-2-(2,4-dimethylphenyl)acetonitrile
-
Substrates: 5.8% conversion
Products: 86% enantiomeric excess
Products: 86% enantiomeric excess
?
HCN + 2,5-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,5-dichlorophenyl)acetonitrile
-
Substrates: 8.8% conversion
Products: 57% enantiomeric excess
Products: 57% enantiomeric excess
?
HCN + 2,5-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,5-dimethoxyphenyl)acetonitrile
-
Substrates: 9% conversion
Products: 63% enantiomeric excess
Products: 63% enantiomeric excess
?
HCN + 2,6-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,6-dichlorophenyl)acetonitrile
-
Substrates: 10% conversion
Products: 12% enantiomeric excess
Products: 12% enantiomeric excess
?
HCN + 2,6-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,6-dimethoxyphenyl)acetonitrile
-
Substrates: 6.5% conversion
Products: 32% enantiomeric excess
Products: 32% enantiomeric excess
?
HCN + 2-allylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-allylcyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-allylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-allylcyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-allyloxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-allyloxycyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-allyloxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-allyloxycyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-butanone
(R)-2-hydroxy-2-methylbutyronitrile
-
Substrates: 48% conversion
Products: 72% enantiomeric excess
Products: 72% enantiomeric excess
?
HCN + 2-decanone
(R)-2-hydroxy-2-methyl-decanenitrile
-
Substrates: 18% conversion
Products: 52% enantiomeric excess
Products: 52% enantiomeric excess
?
HCN + 2-ethoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-ethoxycyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-ethoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-ethoxycyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-ethylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-ethylcyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-ethylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-methylcyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-furancarboxaldehyde
(S)-2-hydroxy-2-(2-furyl)acetonitrile
-
Substrates: 1.2% conversion
Products: 98% enantiomeric excess
Products: 98% enantiomeric excess
?
HCN + 2-heptanone
(R)-2-hydroxy-2-methyl-heptanenitrile
-
Substrates: 39% conversion
Products: 74% enantiomeric excess
Products: 74% enantiomeric excess
?
HCN + 2-hexanone
(R)-2-hydroxy-2-methyl-hexanenitrile
-
Substrates: 48% conversion
Products: 80% enantiomeric excess
Products: 80% enantiomeric excess
?
HCN + 2-methoxybenzaldehyde
(R)-2-hydroxy-2-(2-methoxyphenyl)acetonitrile
-
Substrates: 6.0% conversion
Products: 41% enantiomeric excess
Products: 41% enantiomeric excess
?
HCN + 2-methoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-methoxycyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-methoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-methoxycyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-methylbenzaldehyde
(R)-2-hydroxy-2-(2-methylphenyl)acetonitrile
-
Substrates: 6% conversion
Products: 61% enantiomeric excess
Products: 61% enantiomeric excess
?
HCN + 2-methylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-methylcyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-methylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-methylcyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-n-propoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-n-propoxycyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-n-propoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-n-propoxycyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-n-propylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-n-propylcyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-n-propylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-n-propylcyclohexanecarbonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-naphthalenecarboxaldehyde
(R)-2-hydroxy-2-(2-naphthyl)acetonitrile
-
Substrates: 58% conversion
Products: 98% enantiomeric excess
Products: 98% enantiomeric excess
?
HCN + 2-nonanone
(R)-2-hydroxy-2-methyl-nonanenitrile
-
Substrates: 20% conversion
Products: 65% enantiomeric excess
Products: 65% enantiomeric excess
?
HCN + 2-octanone
(R)-2-hydroxy-2-methyl-octanenitrile
-
Substrates: 22% conversion
Products: 67% enantiomeric excess
Products: 67% enantiomeric excess
?
HCN + 2-pentanone
(R)-2-hydroxy-2-methyl-pentanenitrile
-
Substrates: 46% conversion
Products: 81% enantiomeric excess
Products: 81% enantiomeric excess
?
HCN + 2-pyridinecarboxyaldehyde
(S)-2-hydroxy-2-(2-pyridyl)acetonitrile
-
Substrates: 89% conversion
Products: 22% enantiomeric excess
Products: 22% enantiomeric excess
?
HCN + 2-quinolinecarboxaldehyde
(S)-2-hydroxy-2-(2-quinolinyl)acetonitrile
-
Substrates: 38% conversion
Products: 21% enantiomeric excess
Products: 21% enantiomeric excess
?
HCN + 2-thiophenecarboxaldehyde
(S)-2-hydroxy-2-(2-thiophenyl)acetonitrile
-
Substrates: 31% conversion
Products: 88% enantiomeric excess
Products: 88% enantiomeric excess
?
HCN + 2-trifluoromethylbenzaldehyde
(R)-2-hydroxy-2-(2-trifluoromethylphenyl)acetonitrile
-
Substrates: 72% conversion
Products: 5% enantiomeric excess
Products: 5% enantiomeric excess
?
HCN + 2-undecanone
(R)-2-hydroxy-2-methyl-undecanenitrile
-
Substrates: 21% conversion
Products: 31% enantiomeric excess
Products: 31% enantiomeric excess
?
HCN + 3,3-dimethyl-2-butanone
(R)-2-hydroxy-2,3,3-trimethyl-butyronitrile
-
Substrates: 28% conversion
Products: 38% enantiomeric excess
Products: 38% enantiomeric excess
?
HCN + 3,4,5-trimethoxybenzaldehyde
(R)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)acetonitrile
-
Substrates: 24% conversion
Products: 31% enantiomeric excess
Products: 31% enantiomeric excess
?
HCN + 3,4-dichlorobenzaldehyde
(R)-2-hydroxy-2-(3,4-dichlorophenyl)acetonitrile
-
Substrates: 7.9% conversion
Products: 94% enantiomeric excess
Products: 94% enantiomeric excess
?
HCN + 3,4-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(3,4-dimethoxyphenyl)acetonitrile
-
Substrates: 13% conversion
Products: 78% enantiomeric excess
Products: 78% enantiomeric excess
?
HCN + 3,5-dichlorobenzaldehyde
(R)-2-hydroxy-2-(3,5-dichlorophenyl)acetonitrile
-
Substrates: 21% conversion
Products: 92% enantiomeric excess
Products: 92% enantiomeric excess
?
HCN + 3,5-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(3,5-dimethoxyphenyl)acetonitrile
-
Substrates: 17% conversion
Products: 97% enantiomeric excess
Products: 97% enantiomeric excess
?
HCN + 3-chlorobenzaldehyde
(R)-2-hydroxy-2-(3-chlorophenyl)acetonitrile
-
Substrates: 38% conversion
Products: 92% enantiomeric excess
Products: 92% enantiomeric excess
?
HCN + 3-methoxybenzaldehyde
(R)-2-hydroxy-2-(3-methoxyphenyl)acetonitrile
-
Substrates: 31% conversion
Products: 92% enantiomeric excess
Products: 92% enantiomeric excess
?