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Information on EC 4.1.2.47 - (S)-hydroxynitrile lyase
for references in articles please use BRENDA:EC4.1.2.47
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IUBMB Comments
Hydroxynitrile lyases catalyses the the cleavage of hydroxynitriles into cyanide and the corresponding aldehyde or ketone. In nature the liberation of cyanide serves as a defense mechanism against herbivores and microbial attack in plants. In vitro the enzymes from Manihot esculenta and Hevea brasiliensis accept a broad range of aliphatic and aromatic carbonyl compounds as substrates and catalyse the formation of (S)-hydroxynitriles [1,10].
The enzyme appears in viruses and cellular organisms
- 4.1.2.47
- esculenta
- manihot
- brasiliensis
- hevea
- synthesis
- cassava
- ketone
- hcn
- lyases
- benzaldehyde
-
s-mandelonitrile
- rubber
- athnl
- crantz
-
hydrocyanic
-
s-cyanohydrins
-
r-selective
- arylacetonitrilase
-
s-enantiomer
-
cyanogenesis
- montanum
-
s-mandelic
- pharmacology
- agriculture
- analysis
- drug development
- food industry
Reaction Schemes
show=
+
an aliphatic aldehyde or ketone
Synonyms
mehnl, hbhnl, (s)-hydroxynitrile lyase, alpha-hydroxynitrile lyase, s-hnl, luhnl, hb-hnl, s-selective hydroxynitrile lyase, (s)-oxynitrilase, s-hydroxynitrile lyase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(S)-HbHNL
(S)-Hydroxynitrile lyase
(S)-selective HNL
(S)-selective hydroxynitrile lyase
EC 4.1.2.37
-
-
formerly, part transferred
-
EC 4.1.2.39
Hb-HNL
HbHNL
HNL
Hydroxynitrile lyase
MeHNL
Oxynitrilase
S-HnL
S-hydroxynitrile lyase
S-selective HnL
HNL
-
-
Hydroxynitrile lyase
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
an aromatic (S)-hydroxynitrile = cyanide + an aromatic aldehyde
-
-
-
-
an aliphatic (S)-hydroxynitrile = cyanide + an aliphatic aldehyde or ketone
-
-
-
-
an aliphatic (S)-hydroxynitrile = cyanide + an aliphatic aldehyde or ketone
proposed reaction mechanism: in free enzyme, the hydroxyl group of Ser80 is hydrogen-bonded to the imidazole nitrogen of His236, which in turn is stabilized by a hydrogen bond with Asp208. If the enzyme encounters a substrate molecule, the proton of Ser80 is rapidly transferred to an imidazole nitrogen of His236. The resulting oxyanion of Ser80 functions as a strong base in a nucleophilic attack of the substrate hydroxyl proton, leading to a negatively charged oxyanion on the substrate. This oxyanion could be stabilized by an oxygen hole formed by amide nitrogen of the backbone of Ser80 and Gly78. Both residues belong to the consensus motif, which is typical for nucleophils located in a catalytic triad. The stabilized oxyanion could further increase the local positive charge on the alpha-C atom of the cyanohydrin, allowing the cyanide group to leave the molecule
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
cyanohydrin formation
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
(S)-cyanohydrin lyase (cyanide forming)
Hydroxynitrile lyases catalyses the the cleavage of hydroxynitriles into cyanide and the corresponding aldehyde or ketone. In nature the liberation of cyanide serves as a defense mechanism against herbivores and microbial attack in plants. In vitro the enzymes from Manihot esculenta and Hevea brasiliensis accept a broad range of aliphatic and aromatic carbonyl compounds as substrates and catalyse the formation of (S)-hydroxynitriles [1,10].
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(1S)-1-furan-2-yl-2-nitroethanol
furan-2-carbaldehyde + CH3NO2
-
Substrates: enantiomeric excess: ~90%, yield: 60-70%
Products: -
Products: -
r
(1S)-2-nitro-1-(4-nitrophenyl)ethanol
4-nitrobenzaldehyde + CH3NO2
-
Substrates: enantiomeric excess: ~90%, yield: 60-70%
Products: -
Products: -
r
(1S)-2-nitro-1-phenylethanol
benzaldehyde + CH3NO2
-
Substrates: enantiomeric excess: ~90%, yield: 60-70%
Products: -
Products: -
r
(1S,2R)-2-nitro-1-phenyl-propanol
benzaldehyde + C2H5NO2
-
Substrates: 4 diastereomers, enantiomeric excess: 95%, yield: 67%
Products: -
Products: -
r
(2S)-1-nitrooctan-2-ol
heptanal + CH3NO2
-
Substrates: enantiomeric excess: ~90%, yield: 60-70%
Products: -
Products: -
r
(2S)-2,3-dimethyl-2-hydroxybutyronitrile
?
Substrates: binding mode of the chiral substrates is identical to that observed for the biological substrate 2-hydroxy-2-methylpropanenitrile (i.e. acetone cyanohydrin). Three-point binding mode of the substrates: hydrophobic pocket, hydrogen bonds between the hydroxyl group and Ser80 and Thr11, electrostatic interaction of the cyano group with Lys236
Products: -
Products: -
?
(2S)-2-hydroxy-2-methylpentanenitrile
cyanide + pentan-2-one
Substrates: -
Products: -
Products: -
?
(2S)-hydroxy(3-phenoxyphenyl)ethanenitrile
cyanide + 3-phenoxybenzaldehyde
Substrates: -
Products: -
Products: -
r
(R)-2-(2-furyl)-2-hydroxyacetonitrile
furan-2-carbaldehyde + HCN
-
Substrates: enantiomeric excess: > 99%, yield: 90%
Products: -
Products: -
r
(R)-mandelonitrile
cyanide + benzaldehyde
Substrates: low activity
Products: -
Products: -
r
(S)-2-nitro-1-phenylethanol
benzaldehyde + nitromethane
-
Substrates: -
Products: -
Products: -
r
(S)-2-nitro-1-phenylethanol
nitromethane + benzaldehyde + (R)-2-nitro-1-phenylethanol
-
Substrates: besides the native cyanohydrins reaction, the enzyme also catalyzes the asymmetric reversible Henry reaction yielding (S)-beta-nitroalcohols with high enantiomeric excess. The catalyst productivity achieved during the resolution is 10times higher than that in the HNL-catalyzed synthesis of (S)-2-nitro-1-phenylethanol
Products: -
Products: -
r
(S)-3-phenoxybenzaldehyde cyanohydrin
m-phenoxybenzaldyhyde + HCN
-
Substrates: enantiomeric excess: > 98.5%, yield: 95.5%, used for insecticide synthesis
Products: -
Products: -
r
2-Furylaldehyde + cyanide
Furan-3-yl-hydroxyacetonitrile
-
Substrates: -
Products: -
Products: -
?
2-hydroxy-2-methylpropanenitrile
cyanide + propan-2-one
Substrates: -
Products: -
Products: -
r
2-Methyl-2-hydroxybutyronitrile
Butanone + cyanide
-
Substrates: -
Products: -
Products: -
?
2-nitro-1-phenylethanol
nitromethane + benzaldehyde
Substrates: -
Products: -
Products: -
?
2-Thienylaldehyde + cyanide
Hydroxythiophen-3-yl-acetonitrile
-
Substrates: -
Products: -
Products: -
?
3,3-dimethyl-2-butanone + acetone cyanohydrin
(S)-2-hydroxy-2-methyl-3,3-dimethyl-butyronitrile
-
Substrates: transcyanation
Products: -
Products: -
?
3-[(1S)-1-hydroxy-2-nitroethyl]phenol
3-hydroxybenzaldehyde + CH3NO2
-
Substrates: enantiomeric excess: ~90%, yield: 60-70%
Products: -
Products: -
r
4-Methoxybenzaldehyde + cyanide
4-Methoxymandelonitrile
-
Substrates: -
Products: -
Products: -
?
acetone cyanohydrin
hydrocyanic acid + acetone
Substrates: -
Products: -
Products: -
?
Acetophenone + cyanide
3-Hydroxy-3-phenylpropionitrile
-
Substrates: -
Products: -
Products: -
?
acetyltrimethylsilane + acetone cyanohydrin
(S)-2-trimethylsilyl-2-hydroxyl-propionitrile + acetone
-
Substrates: transcyanation
Products: -
Products: -
?
cyanide + (2E)-3-(4-hydroxyphenyl)prop-2-enal
(2S,3E)-2-hydroxy-4-(4-hydroxyphenyl)but-3-enenitrile
Substrates: -
Products: wild-type enzyme: 95% enantiomeric excess, 80% conversion rate
Products: wild-type enzyme: 95% enantiomeric excess, 80% conversion rate
?
cyanide + (2E)-but-2-enal
(3E)-2-hydroxypent-3-enenitrile
Substrates: -
Products: 86% enantiomeric excess with crude enzyme preparation
Products: 86% enantiomeric excess with crude enzyme preparation
?
cyanide + (2E)-but-2-enal
(3S,3E)-2-hydroxypent-3-enenitrile
Substrates: -
Products: 92% enantiomeric excess
Products: 92% enantiomeric excess
?
cyanide + (2Z)-hex-2-enal
(2S,3Z)-2-hydroxyhept-3-enenitrile
Substrates: -
Products: 80% enantiomeric excess with crude enzyme preparation
Products: 80% enantiomeric excess with crude enzyme preparation
?
cyanide + (4-hydroxyphenyl)acetaldehyde
(2S)-2-hydroxy-3-(4-hydroxyphenyl)propanenitrile
Substrates: -
Products: wild-type enzyme: 96% enantiomeric excess, 88% conversion rate
Products: wild-type enzyme: 96% enantiomeric excess, 88% conversion rate
?
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 48.1% (2S)-hydroxy-[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile and 51.9% (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 48.1% (2S)-hydroxy-[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile and 51.9% (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 52.7% (2S)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 47.3% (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 52.7% (2S)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 47.3% (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 34.9% (2S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 65.1% (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 34.9% (2S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 65.1% (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 35.1% (2S)-hydroxy-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile and 64.9% (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 35.1% (2S)-hydroxy-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile and 64.9% (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 49.9% (2S)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 50.1% (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 49.9% (2S)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 50.1% (2R)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
?
cyanide + 1,1'-diformylferrocene
(R,R)-1,1'-bis(cyanohydroxymethyl)ferrocene
Substrates: a bulky organometallic compound, which does not occur in nature. S-hydroxynitrile lyase from Hevea brasieliensis catalyzes the formation of (R,R)-1,1'-bis(cyanohydroxymethyl)ferrocene at high yield and stereochemical purity
Products: obtained at high yield and stereochemical purity
Products: obtained at high yield and stereochemical purity
?
cyanide + 1,3-benzodioxole-5-carbaldehyde
(2S)-1,3-benzodioxol-5-yl(hydroxy)acetonitrile
Substrates: -
Products: 86% enantiomeric excess
Products: 86% enantiomeric excess
?
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 16.9% (2S)-(2R)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile, 33.0% (2R)-(2R)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile, 18.3% (2S)-(2S)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile and 31.8% (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 16.9% (2S)-(2R)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile, 33.0% (2R)-(2R)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile, 18.3% (2S)-(2S)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile and 31.8% (2R)-(2S)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile
?
cyanide + 1-phenylethanone
(2S)-2-hydroxy-2-phenylpropanenitrile
Substrates: wild-type enzyme: 87% enantiomeric excess, 13% conversion rate
Products: -
Products: -
?
cyanide + 1-phenylpropan-2-one
(2S)-2-hydroxy-2-methyl-3-phenylpropanenitrile
Substrates: wild-type enzyme: 97% enantiomeric excess, 82% conversion rate
Products: -
Products: -
?
cyanide + 2,4-dimethylbenzaldehyde
(2S)-(2,4-dimethylphenyl)(hydroxy)ethanenitrile
Substrates: -
Products: 65% yield, 82% enantiomeric excess
Products: 65% yield, 82% enantiomeric excess
?
cyanide + 2-bromobenzaldehyde
(2S)-(2-bromophenyl)(hydroxy)ethanenitrile
Substrates: -
Products: wild-type enzyme: 96% enantiomeric excess, 96% conversion rate
Products: wild-type enzyme: 96% enantiomeric excess, 96% conversion rate
?
cyanide + 2-bromobenzaldehyde
(S)-2-bromomandelonitrile
Substrates: the (S)-cyanohydrin is formed with more than 99.5% enantiomeric excess
Products: -
Products: -
r
cyanide + 2-chlorobenzaldehyde
(2S)-(2-chlorophenyl)(hydroxy)acetonitrile
Substrates: -
Products: 92% enantiomeric excess
Products: 92% enantiomeric excess
?
cyanide + 2-chlorobenzaldehyde
(2S)-(2-chlorophenyl)(hydroxy)ethanenitrile
Substrates: -
Products: wild-type enzyme: 98% enantiomeric excess, 96% conversion rate
Products: wild-type enzyme: 98% enantiomeric excess, 96% conversion rate
?
cyanide + 2-chlorobenzaldehyde
(S)-2-chloromandelonitrile
Substrates: the (S)-cyanohydrin is formed with more than 99.5% enantiomeric excess
Products: -
Products: -
r
cyanide + 2-flourobenzaldehyde
(S)-2-fluoromandelonitrile
Substrates: the (S)-cyanohydrin is formed with more than 99.5% enantiomeric excess
Products: -
Products: -
r
cyanide + 2-hydroxybenzaldehyde
(2S)-(2-hydroxyphenyl)(hydroxy)ethanenitrile
Substrates: -
Products: wild-type enzyme: 91% enantiomeric excess, 47% conversion rate
Products: wild-type enzyme: 91% enantiomeric excess, 47% conversion rate
?
cyanide + 2-methoxybenzaldehyde
(2S)-2-hydroxy-2-(2-methoxyphenyl)acetonitrile
Substrates: -
Products: 77% enantiomeric excess
Products: 77% enantiomeric excess
?
cyanide + 2-methylbenzaldehyde
(2S)-(2-methylphenyl)(hydroxy)ethanenitrile
Substrates: -
Products: 76% yield, 47% enantiomeric excess
Products: 76% yield, 47% enantiomeric excess
?
cyanide + 3,3-dimethylbutan-2-one
(2S)-2-hydroxy-2,3,3-trimethylbutanenitrile
Substrates: -
Products: 78% enantiomeric excess
Products: 78% enantiomeric excess
?
cyanide + 3-(4-hydroxyphenyl)propanal
(2S)-2-hydroxy-4-(4-hydroxyphenyl)butanenitrile
Substrates: -
Products: wild-type enzyme: 67% enantiomeric excess, 90% conversion rate
Products: wild-type enzyme: 67% enantiomeric excess, 90% conversion rate
?
cyanide + 3-bromobenzaldehyde
(S)-3-bromomandelonitrile
Substrates: the (S)-cyanohydrin is formed with more than 96% enantiomeric excess
Products: -
Products: -
r
cyanide + 3-chlorobenzaldehyde
(S)-3-chloromandelonitrile
Substrates: the (S)-cyanohydrin is formed with more than 96% enantiomeric excess
Products: -
Products: -
r
cyanide + 3-flourobenzaldehyde
(S)-3-fluoromandelonitrile
Substrates: the (S)-cyanohydrin is formed with more than 99% enantiomeric excess
Products: -
Products: -
r
cyanide + 3-hydroxybenzaldehyde
(2S)-(3-hydroxyphenyl)(hydroxy)ethanenitrile
Substrates: -
Products: wild-type enzyme: 97% enantiomeric excess, 88% conversion rate
Products: wild-type enzyme: 97% enantiomeric excess, 88% conversion rate
?
cyanide + 3-methoxybenzaldehyde
(2S)-(3-methoxyphenyl)(hydroxy)ethanenitrile
Substrates: -
Products: 67% yield, 76% enantiomeric excess
Products: 67% yield, 76% enantiomeric excess
?
cyanide + 3-methoxybenzaldehyde
(2S)-2-hydroxy-2-(3-methoxyphenyl)acetonitrile
Substrates: -
Products: 99% enantiomeric excess
Products: 99% enantiomeric excess
?
cyanide + 3-methylbenzaldehyde
(2S)-(3-methylphenyl)(hydroxy)ethanenitrile
Substrates: -
Products: 76% yield, 76% enantiomeric excess
Products: 76% yield, 76% enantiomeric excess
?
cyanide + 3-phenoxybenzaldehyde
(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
Substrates: -
Products: 99% enantiomeric excess
Products: 99% enantiomeric excess
?
cyanide + 3-phenoxybenzaldehyde
(2S)-hydroxy(3-phenoxyphenyl)acetonitrile
Substrates: -
Products: 20% enantiomeric excess
Products: 20% enantiomeric excess
?
cyanide + 3-phenoxybenzaldehyde
(S)-3-phenoxybenzaldehyde cyanohydrin
Substrates: reaction in a high-pH two-phase system
Products: 97% enantiomeric excess
Products: 97% enantiomeric excess
r
cyanide + 3-tetrahydrothiophenone
(S)-3-hydroxytetrahydrothiophene-3-carbonitrile
Substrates: -
Products: -
Products: -
?
cyanide + 4-bromobenzaldehyde
(S)-4-bromomandelonitrile
Substrates: the (S)-cyanohydrin is formed with more than 99.5% enantiomeric excess
Products: -
Products: -
r
cyanide + 4-chlorobenzaldehyde
(S)-4-chloromandelonitrile
Substrates: the (S)-cyanohydrin is formed with 93% enantiomeric excess
Products: -
Products: -
r
cyanide + 4-fluorobenzaldehyde
(S)-4-fluoromandelonitrile
Substrates: the (S)-cyanohydrin is formed with more than 99.5% enantiomeric excess
Products: -
Products: -
r
cyanide + 4-hydroxybenzaldehyde
(2S)-(4-hydroxyphenyl)(hydroxy)ethanenitrile
Substrates: -
Products: wild-type enzyme: 94% enantiomeric excess, 51% conversion rate
Products: wild-type enzyme: 94% enantiomeric excess, 51% conversion rate
?
cyanide + 4-methoxybenzaldehyde
(2S)-(4-methoxyphenyl)(hydroxy)ethanenitrile
Substrates: -
Products: wild-type enzyme: 99% enantiomeric excess, 79% conversion rate
Products: wild-type enzyme: 99% enantiomeric excess, 79% conversion rate
?
cyanide + 4-methoxybenzaldehyde
(2S)-2-hydroxy-2-(4-methoxyphenyl)acetonitrile
Substrates: -
Products: 95% enantiomeric excess
Products: 95% enantiomeric excess
?
cyanide + 4-methoxybenzaldehyde
(2S)-4-methoxymandelonitrile
-
Substrates: -
Products: -
Products: -
?
cyanide + 4-methoxybenzaldehyde
(2S)-hydroxy(4-methoxyphenyl)acetonitrile
Substrates: -
Products: 98% enantiomeric excess
Products: 98% enantiomeric excess
?
cyanide + 4-methoxycyclohex-3-ene-1-carbaldehyde
(2S)-hydroxy[4-(methoxy)cyclohex-3-en-1-yl]ethanenitrile
Substrates: -
Products: -
Products: -
r
cyanide + 4-methylbenzaldehyde
(2S)-(4-methylphenyl)(hydroxy)ethanenitrile
Substrates: -
Products: wild-type enzyme: 99% enantiomeric excess, 50% conversion rate
Products: wild-type enzyme: 99% enantiomeric excess, 50% conversion rate
?
cyanide + 4-methylpentan-2-one
(2S)-2-hydroxy-2,4-dimethylpentanenitrile
Substrates: -
Products: 28% enantiomeric excess
Products: 28% enantiomeric excess
?
cyanide + 4-oxocyclohexanecarbaldehyde
(2S)-hydroxy(4-oxocyclohexyl)ethanenitrile
Substrates: -
Products: -
Products: -
r
cyanide + 4-phenoxybenzaldehyde
(2S)-(4-phenoxyphenyl)(hydroxy)ethanenitrile
Substrates: -
Products: wild-type enzyme: 96% enantiomeric excess, 47% conversion rate
Products: wild-type enzyme: 96% enantiomeric excess, 47% conversion rate
?
cyanide + 4-phenylbutan-2-one
(2S)-2-hydroxy-2-methyl-4-phenylbutanenitrile
Substrates: wild-type enzyme: 49% enantiomeric excess, 36% conversion rate
Products: -
Products: -
?
cyanide + 4-[(trimethylsilyl)oxy]cyclohex-3-ene-1-carbaldehyde
(2S)-hydroxy[4-((trimethylsilyl)oxy)cyclohex-3-en-1-yl]ethanenitrile
Substrates: -
Products: -
Products: -
r
cyanide + 6-methylhept-5-en-2-one
(2S)-2-hydroxy-2,6-dimethylhept-5-enenitrile
Substrates: wild-type enzyme: 61% enantiomeric excess, 78% conversion rate
Products: -
Products: -
?
cyanide + benzaldehyde
(2S)-2-hydroxy-2-phenylacetonitrile
Substrates: -
Products: i.e. (S)-mandelonitrile, more than 99% enantiomeric excess
Products: i.e. (S)-mandelonitrile, more than 99% enantiomeric excess
?
cyanide + butan-2-one
(2S)-2-hydroxy-2-methylbutanenitrile
Substrates: -
Products: 18% enantiomeric excess
Products: 18% enantiomeric excess
?
cyanide + butanal
(2S)-2-hydroxypentanenitrile
Substrates: -
Products: 80% enantiomeric excess
Products: 80% enantiomeric excess
?
cyanide + cinnamaldehyde
(2S)-2-hydroxy-4-phenyl-(E)-but-3-enenitrile
Substrates: -
Products: 95% enantiomeric excess
Products: 95% enantiomeric excess
?
cyanide + cyclohex-3-ene-1-carbaldehyde
(2S)-2-(cyclohex-3-enyl)-2-hydroxyacetonitrile
Substrates: -
Products: 99% enantiomeric excess
Products: 99% enantiomeric excess
?
cyanide + cyclohexanecarbaldehyde
(2S)-2-cyclohexyl-2-hydroxyacetonitrile
Substrates: -
Products: 99% enantiomeric excess
Products: 99% enantiomeric excess
?
cyanide + cyclohexanecarbaldehyde
(2S)-cyclohexyl(hydroxy)acetonitrile
Substrates: -
Products: 92% enantiomeric excess
Products: 92% enantiomeric excess
?
cyanide + decanal
(2S)-2-hydroxyundecanenitrile
Substrates: -
Products: wild-type enzyme: 78% enantiomeric excess, 65% conversion rate
Products: wild-type enzyme: 78% enantiomeric excess, 65% conversion rate
?
cyanide + dodecanal
(2S)-2-hydroxytridecanenitrile
Substrates: -
Products: wild-type enzyme: 71% enantiomeric excess, 80% conversion rate
Products: wild-type enzyme: 71% enantiomeric excess, 80% conversion rate
?
cyanide + ferrocenecarboxaldehyde
(R)-(cyanohydroxymethyl)ferrocene
Substrates: i.e. bis(cyclopentadienyl)iron, a bulky organometallic compound, which does not occur in nature. S-hydroxynitrile lyase from Hevea brasiliensis catalyzes the formation of (R)-(cyanohydroxymethyl)ferrocene at high yield and stereochemical purity
Products: obtained at high yield and stereochemical purity
Products: obtained at high yield and stereochemical purity
?
cyanide + heptan-2-one
(2S)-2-hydroxy-2-methylheptanenitrile
Substrates: -
Products: 92% enantiomeric excess
Products: 92% enantiomeric excess
?
cyanide + heptan-3-one
(2S)-2-ethyl-2-hydroxyhexanenitrile
Substrates: wild-type enzyme: 46% enantiomeric excess, 14% conversion rate
Products: -
Products: -
?
cyanide + hexan-2-one
(2S)-2-hydroxy-2-methylhexanenitrile
Substrates: -
Products: 80% enantiomeric excess
Products: 80% enantiomeric excess
?
cyanide + hexanal
2-hydroxyheptanenitrile
Substrates: -
Products: 84% enantiomeric excess
Products: 84% enantiomeric excess
?
cyanide + nonanal
(2S)-2-hydroxydecanenitrile
Substrates: -
Products: wild-type enzyme: 80% enantiomeric excess, 99% conversion rate
Products: wild-type enzyme: 80% enantiomeric excess, 99% conversion rate
?
cyanide + nonanal
2-hydroxydecanenitrile
Substrates: -
Products: 85% enantiomeric excess
Products: 85% enantiomeric excess
?
cyanide + octan-3-one
(2S)-2-ethyl-2-hydroxyheptanenitrile
Substrates: wild-type enzyme: 61% enantiomeric excess, 24% conversion rate
Products: -
Products: -
?
cyanide + octanal
(2S)-2-hydroxynonanenitrile
Substrates: -
Products: wild-type enzyme: 79% enantiomeric excess, 96% conversion rate
Products: wild-type enzyme: 79% enantiomeric excess, 96% conversion rate
?
cyanide + pentan-2-one
(2S)-2-hydroxy-2-methylpentanenitrile
Substrates: -
Products: 69% enantiomeric excess
Products: 69% enantiomeric excess
?
cyanide + pentanal
(2S)-2-hydroxyhexanenitrile
Substrates: -
Products: 91% enantiomeric excess
Products: 91% enantiomeric excess
?
cyanide + phenylacetaldehyde
(2S)-2-hydroxy-3-phenylpropanenitrile
Substrates: -
Products: 99% enantiomeric excess
Products: 99% enantiomeric excess
?
cyanide + phenylacetaldehyde
2-hydroxy-3-phenylpropanenitrile
Substrates: -
Products: wild-type enzyme: 98% enantiomeric excess, 99% conversion rate
Products: wild-type enzyme: 98% enantiomeric excess, 99% conversion rate
?
cyanide + piperonal
?
Substrates: -
Products: 47% yield, 74% enantiomeric excess
Products: 47% yield, 74% enantiomeric excess
?
cyanide + prop-2-enal
(2S)-2-hydroxy-3-methylbutanenitrile
-
Substrates: -
Products: -
Products: -
?
cyanide + prop-2-enal
2-hydroxybut-3-enenitrile
Substrates: -
Products: 84% enantiomeric excess
Products: 84% enantiomeric excess
?
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 5.4% (2S)-hydroxy-[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile, 45.9% (2R)-hydroxy-[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile, 3.9% (2S)-hydroxy[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile and 44.9% (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 5.4% (2S)-hydroxy-[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile, 45.9% (2R)-hydroxy-[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile, 3.9% (2S)-hydroxy[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile and 44.9% (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 17.1% (2S)-hydroxy-[(2R)-tetrahydrofuran-2-yl]ethanenitrile, 32.9% (2R)-hydroxy-[(2R)-tetrahydrofuran-2-yl]ethanenitrile, 18.9% (2S)-hydroxy[(2S)-tetrahydrofuran-2-yl]ethanenitrile and 31.1% (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 17.1% (2S)-hydroxy-[(2R)-tetrahydrofuran-2-yl]ethanenitrile, 32.9% (2R)-hydroxy-[(2R)-tetrahydrofuran-2-yl]ethanenitrile, 18.9% (2S)-hydroxy[(2S)-tetrahydrofuran-2-yl]ethanenitrile and 31.1% (2R)-hydroxy[(2S)-tetrahydrofuran-2-yl]ethanenitrile
?
cyanide + thiophene-2-carbaldehyde
(2S)-hydroxy(thiophen-2-yl)ethanenitrile
-
Substrates: -
Products: -
Products: -
?
ferrocenyl aldehyde + HCN
ferrocenyl-cyanohydrin
Substrates: -
Products: -
Products: -
?
furan-3-carbaldehyde + HCN
(2S)-hydroxy(furan-3-yl)ethanenitrile
Substrates: -
Products: 92% enantiomeric excess
Products: 92% enantiomeric excess
?
HCN + (2E)-oct-2-enal
(2S,3E)-2-hydroxynon-3-enenitrile
-
Substrates: -
Products: -
Products: -
?
HCN + (benzyloxy)acetaldehyde
3-(benzyloxy)-(2S)-2-hydroxy-propanenitrile + 3-(benzyloxy)-(2R)-2-hydroxy-propanenitrile
-
Substrates: -
Products: 50% 3-(benzyloxy)-(2S)-2-hydroxy-propanenitrile and 50% 3-(benzyloxy)-(2R)-2-hydroxy-propanenitrile
Products: 50% 3-(benzyloxy)-(2S)-2-hydroxy-propanenitrile and 50% 3-(benzyloxy)-(2R)-2-hydroxy-propanenitrile
?
HCN + (E)-2-butenal
(3E)-2-hydroxypent-3-enenitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 1,1'-diformylferrocene
(R,R)-1,1-bis(cyanohydroxymethyl)ferrocene
-
Substrates: -
Products: -
Products: -
?
HCN + 2,2-dimethylpropanal
2-hydroxy-3,3-dimethylbutyronitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-allyloxybutanal
3-allyloxy-2-hydroxypentanenitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-allyloxyheptanal
(2R,3RS)-3-allyloxy-2-hydroxyoctanenitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-allyloxyhexanal
(2R,3RS)-3-allyloxy-2-hydroxyheptanenitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-allyloxypentanal
(2R,3RS)-3-allyloxy-2-hydroxyhexanenitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-allyloxypropanal
3-allyloxy-2-hydroxybutanenitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-benzyloxypropanal
3-benzyloxy-2-hydroxybutanenitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-chlorobenzaldehyde
(2-chlorophenyl)(hydroxy)acetonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-methoxymethoxypropanal
3-methoxymethoxy-2-hydroxybutanenitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-methylallyloxyacetaldehyde
3-(2-methylallyloxy)-2-hydroxypropionitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 2-methyldihydrofuran
3-hydroxy-2-methyltetrahydrofuran-3-carbonitrile
-
Substrates: analysis of diastereomeric distribution of the products, depending on different reaction conditions such as pH, reaction time, and solvent properties
Products: -
Products: -
?
HCN + 2-methyldihydrothiophen-3(2H)-one
3-hydroxy-2-methyltetrahydrothiophen-3-carbonitrile
-
Substrates: analysis of diastereomeric distribution of the products, depending on different reaction conditions such as pH, reaction time, and solvent properties
Products: -
Products: -
?
HCN + 2-naphthaldehyde
(2S)-2-hydroxynaphthalen-2-yl-acetonitrile + (2R)-2-hydroxynaphthalen-2-yl-acetonitrile
-
Substrates: -
Products: 83% (2S)-2-hydroxynaphthalen-2-yl-acetonitrile and 17% (2R)-2-hydroxynaphthalen-2-yl-acetonitrile
Products: 83% (2S)-2-hydroxynaphthalen-2-yl-acetonitrile and 17% (2R)-2-hydroxynaphthalen-2-yl-acetonitrile
?
HCN + 2-naphthylacetaldehyde
(2S)-2-hydroxy-3-naphthalen-1-yl-propionitrile + (2R)-2-hydroxy-3-naphthalen-1-yl-propionitrile
-
Substrates: -
Products: 84.3% (2S)-2-hydroxy-3-naphthalen-1-yl-propionitrile and 15.6% (2R)-2-hydroxy-3-naphthalen-1-yl-propionitrile
Products: 84.3% (2S)-2-hydroxy-3-naphthalen-1-yl-propionitrile and 15.6% (2R)-2-hydroxy-3-naphthalen-1-yl-propionitrile
?
HCN + 3-furaldehyde
(2R)-3-furyl(hydroxy)acetonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 3-furylcarbaldehyde
hydroxy(fur-3yl)acetonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 3-phenoxybenzaldehyde
(2S)-hydroxy(3-phenoxyphenyl)acetonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + 3-phenoxypropanal
(2S)-2-hydroxy-4-phenoxybutanenitrile + (2S)-2-hydroxy-4-phenoxybutanenitrile
-
Substrates: -
Products: 95.8% (2S)-2-hydroxy-4-phenoxybutanenitrile and 4.2% (2R)-2-hydroxy-4-phenoxybutanenitrile
Products: 95.8% (2S)-2-hydroxy-4-phenoxybutanenitrile and 4.2% (2R)-2-hydroxy-4-phenoxybutanenitrile
?
HCN + 4-methoxybenzaldehyde
(4-methoxyphenyl) (hydroxy)acetonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + allyloxy-2-hydroxypropionitrile
3-allyloxy-2-hydroxypropionitrile
-
Substrates: -
Products: -
Products: -
?
HCN + benzyloxyacetaldehyde
3-benzyloxy-2-hydroxypropionitrile
-
Substrates: -
Products: -
Products: -
?
HCN + cyclohexanecarbaldehyde
(2R)-cyclohexyl(hydroxy)acetonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + decanal
(S)-2-hydroxyundecanenitrile
-
Substrates: reaction in a two phase solvent system aqueous buffer and ionic liquid. Compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remains good
Products: -
Products: -
?
HCN + dodecanal
(S)-2-hydroxytridecanenitrile
-
Substrates: reaction in a two phase solvent system aqueous buffer and ionic liquid. Compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remains good
Products: -
Products: -
?
HCN + formylferrocene
(R)-(cyanohydroxymethyl)ferrocene
-
Substrates: -
Products: -
Products: -
?
HCN + furaldehyde
(2R)-furan-2-yl(hydroxy)ethanenitrile
-
Substrates: enzyme encapsulated in sol-gel matrix
Products: -
Products: -
?
HCN + hexanal
(S)-2-hydroxyoctanenitrile
-
Substrates: enzyme encapsulated in sol-gel matrix
Products: -
Products: -
?
HCN + isobutyraldehyde
2-hydroxy-3-methylbutyronitrile
-
Substrates: -
Products: -
Products: -
?
HCN + m-phenoxybenzaldehyde
(S)-hydroxy-(3-phenoxy-phenyl)acetonitrile
-
Substrates: enzyme encapsulated in sol-gel matrix
Products: -
Products: -
?
HCN + methoxymethoxyacetaldehyde
2-hydroxy-3-methoxymethoxypropionitrile
-
Substrates: -
Products: -
Products: -
?
HCN + methyl isopropyl ketone
(S)-2-hydroxy-2,3-dimethylbutanenitrile
-
Substrates: enzyme encapsulated in sol-gel matrix
Products: -
Products: -
?
HCN + phenylacetaldehyde
(2R)-2-hydroxy-3-phenylpropanenitrile
-
Substrates: -
Products: -
Products: -
?
HCN + rac-2-methyl-3-phenylpropionaldehyde
(2S,3R)-2-hydroxy-3-methyl-4-phenylbutyronitrile
-
Substrates: -
Products: wild-type and mutant enzymes Y128Y, W128L, W128C, W128A are (S)-selective
Products: wild-type and mutant enzymes Y128Y, W128L, W128C, W128A are (S)-selective
?
HCN + rac-2-phenylbutyraldehyde
2-hydroxy-3-phenylpentanenitrile
-
Substrates: -
Products: diastereomer composition. (2R,3R): 0.5% (wild-type), 0.7% (mutant W128Y), 0.8% (mutant W128L), 0.4% (mutant W128L), 0.6% (mutant W128C), 0% (mutant W128A). (2R,3S): 4.5% (wild-type), 4.6% (mutant W128Y), 24.3% (mutant W128L), 23.4% (mutant W128C), 34.1% (mutant W128A), 35.5% (mutant W128V). (2S,3S): 45.8% (wild-type), 45.6% (mutant W128Y), 25.1% (mutant W128L), 26.1% (mutant W128C), 15.0% (mutant W128A), 13.7% (mutant W128V). (2S,3R): 49.2% (wild-type), 49.1% (mutant W128Y), 49.8% (mutant W128L), 50.1% (mutant W128C), 50.3% (mutant W128A), 50.8% (mutant W128V)
Products: diastereomer composition. (2R,3R): 0.5% (wild-type), 0.7% (mutant W128Y), 0.8% (mutant W128L), 0.4% (mutant W128L), 0.6% (mutant W128C), 0% (mutant W128A). (2R,3S): 4.5% (wild-type), 4.6% (mutant W128Y), 24.3% (mutant W128L), 23.4% (mutant W128C), 34.1% (mutant W128A), 35.5% (mutant W128V). (2S,3S): 45.8% (wild-type), 45.6% (mutant W128Y), 25.1% (mutant W128L), 26.1% (mutant W128C), 15.0% (mutant W128A), 13.7% (mutant W128V). (2S,3R): 49.2% (wild-type), 49.1% (mutant W128Y), 49.8% (mutant W128L), 50.1% (mutant W128C), 50.3% (mutant W128A), 50.8% (mutant W128V)
?
HCN + rac-2-phenylpropionaldehyde
2-hydroxy-3-phenylbutyronitrile
-
Substrates: -
Products: diastereomer composition. (2R,3R): 0.1% (wild-type), 0.2% (mutant W128Y), 0.3% (mutant W128L), 0.5% (mutant W128C), 1% (mutant W128A). (2R,3S): 5.2% (wild-type), 24.4% (mutant W128Y), 37.5% (mutant W128L), 43.4% (mutant W128C), 46.2% mutant (W128A). (2S,3S): 44.4% (wild-type), 25.4% (mutant W128Y), 12.2% (mutant W128C), 6.1% (mutant W128L), 3.4% (mutant W128A). (2S,3R): 50.3% (wild-type), 50.2% (mutant W128Y), 50.0% (mutant W128L), 50.0% (mutant W128C), 49.4% (mutant W128A)
Products: diastereomer composition. (2R,3R): 0.1% (wild-type), 0.2% (mutant W128Y), 0.3% (mutant W128L), 0.5% (mutant W128C), 1% (mutant W128A). (2R,3S): 5.2% (wild-type), 24.4% (mutant W128Y), 37.5% (mutant W128L), 43.4% (mutant W128C), 46.2% mutant (W128A). (2S,3S): 44.4% (wild-type), 25.4% (mutant W128Y), 12.2% (mutant W128C), 6.1% (mutant W128L), 3.4% (mutant W128A). (2S,3R): 50.3% (wild-type), 50.2% (mutant W128Y), 50.0% (mutant W128L), 50.0% (mutant W128C), 49.4% (mutant W128A)
?
HCN + rac-3-phenylbutyraldehyde
(2S,3R)-2-hydroxy-4-phenylpentanenitrile
-
Substrates: -
Products: wild-type and mutant enzymes Y128Y, W128L, W128C, W128A are (S)-selective
Products: wild-type and mutant enzymes Y128Y, W128L, W128C, W128A are (S)-selective
?
HCN + tetrahydro-2H-3-pyranone
(3R)-3-hydroxytetrahydro-2H-pyran-3-carbonitrile
-
Substrates: -
Products: enantiomeric excess at pH 4.75 is 48.3%
Products: enantiomeric excess at pH 4.75 is 48.3%
?
HCN + tetrahydro-3-furanone
(3R)-3-hydroxytetrahydrofuran-3-carbonitrile
-
Substrates: -
Products: 81% enantiomeric excess
Products: 81% enantiomeric excess
?
HCN + thiophen-2-carbaldehyde
hydroxy(thien-2-yl)acetonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + thiophen-3-carbaldehyde
hydroxy(thien-3-yl)acetonitrile
-
Substrates: -
Products: -
Products: -
?
HCN + undecanal
(S)-2-hydroxydodecanenitrile
-
Substrates: reaction in a two phase solvent system aqueous buffer and ionic liquid. Compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remains good
Products: -
Products: -
?
Isobutyraldehyde + cyanide
2-Hydroxy-3-methylbutyronitrile
-
Substrates: -
Products: -
Products: -
?
m-phenoxybenzaldehyde cyanohydrin
m-phenoxybenzaldehyde + cyanide
Substrates: 2-phenoxybenzaldehyde cyanohydrin is converted with lower activity than (S)-mandelonitrile and cyclohexanone cyanohydrile
Products: -
Products: -
?
m-phenoxybenzaldehyde cyanohydrin
m-phenoxybenzaldehyde + HCN