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(1S)-1-furan-2-yl-2-nitroethanol
furan-2-carbaldehyde + CH3NO2
-
enantiomeric excess: ~90%, yield: 60-70%
-
-
r
(1S)-2-nitro-1-(4-nitrophenyl)ethanol
4-nitrobenzaldehyde + CH3NO2
-
enantiomeric excess: ~90%, yield: 60-70%
-
-
r
(1S)-2-nitro-1-phenylethanol
benzaldehyde + CH3NO2
-
enantiomeric excess: ~90%, yield: 60-70%
-
-
r
(1S,2R)-2-nitro-1-phenyl-propanol
benzaldehyde + C2H5NO2
-
4 diastereomers, enantiomeric excess: 95%, yield: 67%
-
-
r
(2S)-1-nitrooctan-2-ol
heptanal + CH3NO2
-
enantiomeric excess: ~90%, yield: 60-70%
-
-
r
(2S)-2,3-dimethyl-2-hydroxybutyronitrile
?
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
-
-
?
(2S)-2-hydroxy-2-methylbutanenitrile
cyanide + butan-2-one
(2S)-2-hydroxy-2-methylpentanenitrile
cyanide + pentan-2-one
-
-
-
?
(2S)-hydroxy(3-phenoxyphenyl)ethanenitrile
cyanide + 3-phenoxybenzaldehyde
-
-
-
r
(R)-2-(2-furyl)-2-hydroxyacetonitrile
furan-2-carbaldehyde + HCN
-
enantiomeric excess: > 99%, yield: 90%
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
low activity
-
-
r
(S)-2-nitro-1-phenylethanol
benzaldehyde + nitromethane
-
-
-
-
r
(S)-2-nitro-1-phenylethanol
nitromethane + benzaldehyde + (R)-2-nitro-1-phenylethanol
-
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
-
-
r
(S)-3-phenoxybenzaldehyde cyanohydrin
m-phenoxybenzaldyhyde + HCN
-
enantiomeric excess: > 98.5%, yield: 95.5%, used for insecticide synthesis
-
-
r
(S)-mandelonitrile
benzaldehyde + HCN
(S)-mandelonitrile
cyanide + benzaldehyde
(S)-mandelonitrile
HCN + benzaldehyde
2-furaldehyde cyanohydrin
2-furaldehyde + HCN
2-Furylaldehyde + cyanide
Furan-3-yl-hydroxyacetonitrile
-
-
-
-
?
2-hydroxy-2-methylpropanenitrile
acetone + HCN
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
2-hydroxy-2-methylpropanenitrile
cyanide + propan-2-one
-
-
-
r
2-hydroxy-2-methylpropanenitrile
HCN + acetone
2-hydroxyisobutyronitrile
HCN + acetone
-
-
-
?
2-Methyl-2-hydroxybutyronitrile
Butanone + cyanide
-
-
-
?
2-nitro-1-phenylethanol
?
2-nitro-1-phenylethanol
nitromethane + benzaldehyde
-
-
-
?
2-Pentanone + cyanide
3-Hydroxyhexanonitrile
-
-
-
-
?
2-Thienylaldehyde + cyanide
Hydroxythiophen-3-yl-acetonitrile
-
-
-
-
?
3,3-dimethyl-2-butanone + acetone cyanohydrin
(S)-2-hydroxy-2-methyl-3,3-dimethyl-butyronitrile
-
transcyanation
-
-
?
3-[(1S)-1-hydroxy-2-nitroethyl]phenol
3-hydroxybenzaldehyde + CH3NO2
-
enantiomeric excess: ~90%, yield: 60-70%
-
-
r
4-Methoxybenzaldehyde + cyanide
4-Methoxymandelonitrile
-
-
-
-
?
Acetone cyanhydrin
Cyanide + acetone
acetone cyanhydrin
HCN + acetone
acetone cyanohydrin
cyanide + acetone
acetone cyanohydrin
hydrocyanic acid + acetone
-
-
-
?
Acetophenone + cyanide
3-Hydroxy-3-phenylpropionitrile
-
-
-
-
?
acetyltrimethylsilane + acetone cyanohydrin
(S)-2-trimethylsilyl-2-hydroxyl-propionitrile + acetone
-
transcyanation
-
-
?
Benzaldehyde + cyanide
(S)-Mandelonitrile
-
-
-
-
?
benzaldehyde + HCN
(S)-mandelonitrile
-
-
-
?
cyanide + (2E)-3-(4-hydroxyphenyl)prop-2-enal
(2S,3E)-2-hydroxy-4-(4-hydroxyphenyl)but-3-enenitrile
-
wild-type enzyme: 95% enantiomeric excess, 80% conversion rate
-
?
cyanide + (2E)-but-2-enal
(3E)-2-hydroxypent-3-enenitrile
-
86% enantiomeric excess with crude enzyme preparation
-
?
cyanide + (2E)-but-2-enal
(3S,3E)-2-hydroxypent-3-enenitrile
-
92% enantiomeric excess
-
?
cyanide + (2E)-hex-2-enal
(2S,3E)-2-hydroxyhept-3-enenitrile
cyanide + (2Z)-hex-2-enal
(2S,3Z)-2-hydroxyhept-3-enenitrile
-
80% enantiomeric excess with crude enzyme preparation
-
?
cyanide + (4-hydroxyphenyl)acetaldehyde
(2S)-2-hydroxy-3-(4-hydroxyphenyl)propanenitrile
-
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
-
-
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
-
-
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
-
-
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
-
-
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
-
-
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
-
-
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
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
obtained at high yield and stereochemical purity
-
?
cyanide + 1,3-benzodioxole-5-carbaldehyde
(2S)-1,3-benzodioxol-5-yl(hydroxy)acetonitrile
-
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
-
-
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-naphthalene carboxaldehyde
?
cyanide + 1-phenylethanone
(2S)-2-hydroxy-2-phenylpropanenitrile
wild-type enzyme: 87% enantiomeric excess, 13% conversion rate
-
-
?
cyanide + 1-phenylpropan-2-one
(2S)-2-hydroxy-2-methyl-3-phenylpropanenitrile
wild-type enzyme: 97% enantiomeric excess, 82% conversion rate
-
-
?
cyanide + 2,2-dimethylpropanal
(2S)-2-hydroxy-3,3-dimethylbutanenitrile
cyanide + 2,4-dimethylbenzaldehyde
(2S)-(2,4-dimethylphenyl)(hydroxy)ethanenitrile
-
65% yield, 82% enantiomeric excess
-
?
cyanide + 2-bromobenzaldehyde
(2S)-(2-bromophenyl)(hydroxy)ethanenitrile
-
wild-type enzyme: 96% enantiomeric excess, 96% conversion rate
-
?
cyanide + 2-bromobenzaldehyde
(S)-2-bromomandelonitrile
the (S)-cyanohydrin is formed with more than 99.5% enantiomeric excess
-
-
r
cyanide + 2-chlorobenzaldehyde
(2S)-(2-chlorophenyl)(hydroxy)acetonitrile
-
92% enantiomeric excess
-
?
cyanide + 2-chlorobenzaldehyde
(2S)-(2-chlorophenyl)(hydroxy)ethanenitrile
-
wild-type enzyme: 98% enantiomeric excess, 96% conversion rate
-
?
cyanide + 2-chlorobenzaldehyde
(S)-2-chloromandelonitrile
the (S)-cyanohydrin is formed with more than 99.5% enantiomeric excess
-
-
r
cyanide + 2-flourobenzaldehyde
(S)-2-fluoromandelonitrile
the (S)-cyanohydrin is formed with more than 99.5% enantiomeric excess
-
-
r
cyanide + 2-hydroxybenzaldehyde
(2S)-(2-hydroxyphenyl)(hydroxy)ethanenitrile
-
wild-type enzyme: 91% enantiomeric excess, 47% conversion rate
-
?
cyanide + 2-methoxybenzaldehyde
(2S)-2-hydroxy-2-(2-methoxyphenyl)acetonitrile
-
77% enantiomeric excess
-
?
cyanide + 2-methylbenzaldehyde
(2S)-(2-methylphenyl)(hydroxy)ethanenitrile
-
76% yield, 47% enantiomeric excess
-
?
cyanide + 2-methylpropanal
(2S)-2-hydroxy-3-methylbutanenitrile
cyanide + 2-thiophene carboxaldehyde
?
cyanide + 3,3-dimethylbutan-2-one
(2S)-2-hydroxy-2,3,3-trimethylbutanenitrile
-
78% enantiomeric excess
-
?
cyanide + 3-(4-hydroxyphenyl)propanal
(2S)-2-hydroxy-4-(4-hydroxyphenyl)butanenitrile
-
wild-type enzyme: 67% enantiomeric excess, 90% conversion rate
-
?
cyanide + 3-bromobenzaldehyde
(S)-3-bromomandelonitrile
the (S)-cyanohydrin is formed with more than 96% enantiomeric excess
-
-
r
cyanide + 3-chlorobenzaldehyde
(S)-3-chloromandelonitrile
the (S)-cyanohydrin is formed with more than 96% enantiomeric excess
-
-
r
cyanide + 3-flourobenzaldehyde
(S)-3-fluoromandelonitrile
the (S)-cyanohydrin is formed with more than 99% enantiomeric excess
-
-
r
cyanide + 3-hydroxybenzaldehyde
(2S)-(3-hydroxyphenyl)(hydroxy)ethanenitrile
-
wild-type enzyme: 97% enantiomeric excess, 88% conversion rate
-
?
cyanide + 3-methoxybenzaldehyde
(2S)-(3-methoxyphenyl)(hydroxy)ethanenitrile
-
67% yield, 76% enantiomeric excess
-
?
cyanide + 3-methoxybenzaldehyde
(2S)-2-hydroxy-2-(3-methoxyphenyl)acetonitrile
-
99% enantiomeric excess
-
?
cyanide + 3-methylbenzaldehyde
(2S)-(3-methylphenyl)(hydroxy)ethanenitrile
-
76% yield, 76% enantiomeric excess
-
?
cyanide + 3-phenoxybenzaldehyde
(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
-
99% enantiomeric excess
-
?
cyanide + 3-phenoxybenzaldehyde
(2S)-hydroxy(3-phenoxyphenyl)acetonitrile
-
20% enantiomeric excess
-
?
cyanide + 3-phenoxybenzaldehyde
(S)-3-phenoxybenzaldehyde cyanohydrin
reaction in a high-pH two-phase system
97% enantiomeric excess
-
r
cyanide + 3-phenylpropanal
(2S)-2-hydroxy-4-phenylbutanenitrile
cyanide + 3-tetrahydrothiophenone
(S)-3-hydroxytetrahydrothiophene-3-carbonitrile
-
-
-
?
cyanide + 4-biphenyl carboxaldehyde
?
cyanide + 4-bromobenzaldehyde
(S)-4-bromomandelonitrile
the (S)-cyanohydrin is formed with more than 99.5% enantiomeric excess
-
-
r
cyanide + 4-chlorobenzaldehyde
(S)-4-chloromandelonitrile
the (S)-cyanohydrin is formed with 93% enantiomeric excess
-
-
r
cyanide + 4-fluorobenzaldehyde
(S)-4-fluoromandelonitrile
the (S)-cyanohydrin is formed with more than 99.5% enantiomeric excess
-
-
r
cyanide + 4-hydroxybenzaldehyde
(2S)-(4-hydroxyphenyl)(hydroxy)ethanenitrile
-
wild-type enzyme: 94% enantiomeric excess, 51% conversion rate
-
?
cyanide + 4-methoxybenzaldehyde
(2S)-(4-methoxyphenyl)(hydroxy)ethanenitrile
-
wild-type enzyme: 99% enantiomeric excess, 79% conversion rate
-
?
cyanide + 4-methoxybenzaldehyde
(2S)-2-hydroxy-2-(4-methoxyphenyl)acetonitrile
-
95% enantiomeric excess
-
?
cyanide + 4-methoxybenzaldehyde
(2S)-4-methoxymandelonitrile
-
-
-
-
?
cyanide + 4-methoxybenzaldehyde
(2S)-hydroxy(4-methoxyphenyl)acetonitrile
-
98% enantiomeric excess
-
?
cyanide + 4-methoxycyclohex-3-ene-1-carbaldehyde
(2S)-hydroxy[4-(methoxy)cyclohex-3-en-1-yl]ethanenitrile
-
-
-
r
cyanide + 4-methylbenzaldehyde
(2S)-(4-methylphenyl)(hydroxy)ethanenitrile
-
wild-type enzyme: 99% enantiomeric excess, 50% conversion rate
-
?
cyanide + 4-methylpentan-2-one
(2S)-2-hydroxy-2,4-dimethylpentanenitrile
-
28% enantiomeric excess
-
?
cyanide + 4-oxocyclohexanecarbaldehyde
(2S)-hydroxy(4-oxocyclohexyl)ethanenitrile
-
-
-
r
cyanide + 4-phenoxybenzaldehyde
(2S)-(4-phenoxyphenyl)(hydroxy)ethanenitrile
-
wild-type enzyme: 96% enantiomeric excess, 47% conversion rate
-
?
cyanide + 4-phenylbutan-2-one
(2S)-2-hydroxy-2-methyl-4-phenylbutanenitrile
wild-type enzyme: 49% enantiomeric excess, 36% conversion rate
-
-
?
cyanide + 4-[(trimethylsilyl)oxy]cyclohex-3-ene-1-carbaldehyde
(2S)-hydroxy[4-((trimethylsilyl)oxy)cyclohex-3-en-1-yl]ethanenitrile
-
-
-
r
cyanide + 6-methylhept-5-en-2-one
(2S)-2-hydroxy-2,6-dimethylhept-5-enenitrile
wild-type enzyme: 61% enantiomeric excess, 78% conversion rate
-
-
?
cyanide + benzaldehyde
(2S)-2-hydroxy-2-phenylacetonitrile
-
i.e. (S)-mandelonitrile, more than 99% enantiomeric excess
-
?
cyanide + benzaldehyde
(S)-mandelonitrile
cyanide + butan-2-one
(2S)-2-hydroxy-2-methylbutanenitrile
-
18% enantiomeric excess
-
?
cyanide + butanal
(2S)-2-hydroxypentanenitrile
-
80% enantiomeric excess
-
?
cyanide + cinnamaldehyde
(2S)-2-hydroxy-4-phenyl-(E)-but-3-enenitrile
-
95% enantiomeric excess
-
?
cyanide + cyclohex-3-ene-1-carbaldehyde
(2S)-2-(cyclohex-3-enyl)-2-hydroxyacetonitrile
-
99% enantiomeric excess
-
?
cyanide + cyclohexanecarbaldehyde
(2S)-2-cyclohexyl-2-hydroxyacetonitrile
-
99% enantiomeric excess
-
?
cyanide + cyclohexanecarbaldehyde
(2S)-cyclohexyl(hydroxy)acetonitrile
-
92% enantiomeric excess
-
?
cyanide + decanal
(2S)-2-hydroxyundecanenitrile
-
wild-type enzyme: 78% enantiomeric excess, 65% conversion rate
-
?
cyanide + dodecanal
(2S)-2-hydroxytridecanenitrile
-
wild-type enzyme: 71% enantiomeric excess, 80% conversion rate
-
?
cyanide + ferrocenecarboxaldehyde
(R)-(cyanohydroxymethyl)ferrocene
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
obtained at high yield and stereochemical purity
-
?
cyanide + heptan-2-one
(2S)-2-hydroxy-2-methylheptanenitrile
-
92% enantiomeric excess
-
?
cyanide + heptan-3-one
(2S)-2-ethyl-2-hydroxyhexanenitrile
wild-type enzyme: 46% enantiomeric excess, 14% conversion rate
-
-
?
cyanide + hexan-2-one
(2S)-2-hydroxy-2-methylhexanenitrile
-
80% enantiomeric excess
-
?
cyanide + hexanal
2-hydroxyheptanenitrile
-
84% enantiomeric excess
-
?
cyanide + nonanal
(2S)-2-hydroxydecanenitrile
-
wild-type enzyme: 80% enantiomeric excess, 99% conversion rate
-
?
cyanide + nonanal
2-hydroxydecanenitrile
-
85% enantiomeric excess
-
?
cyanide + octan-3-one
(2S)-2-ethyl-2-hydroxyheptanenitrile
wild-type enzyme: 61% enantiomeric excess, 24% conversion rate
-
-
?
cyanide + octanal
(2S)-2-hydroxynonanenitrile
-
wild-type enzyme: 79% enantiomeric excess, 96% conversion rate
-
?
cyanide + pentan-2-one
(2S)-2-hydroxy-2-methylpentanenitrile
-
69% enantiomeric excess
-
?
cyanide + pentanal
(2S)-2-hydroxyhexanenitrile
-
91% enantiomeric excess
-
?
cyanide + phenylacetaldehyde
(2S)-2-hydroxy-3-phenylpropanenitrile
-
99% enantiomeric excess
-
?
cyanide + phenylacetaldehyde
2-hydroxy-3-phenylpropanenitrile
-
wild-type enzyme: 98% enantiomeric excess, 99% conversion rate
-
?
cyanide + piperonal
?
-
47% yield, 74% enantiomeric excess
-
?
cyanide + prop-2-enal
(2S)-2-hydroxy-3-methylbutanenitrile
-
-
-
-
?
cyanide + prop-2-enal
(2S)-2-hydroxybut-3-enenitrile
cyanide + prop-2-enal
2-hydroxybut-3-enenitrile
-
84% enantiomeric excess
-
?
cyanide + propanal
(2S)-2-hydroxybutanenitrile
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 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
-
-
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
-
-
-
-
?
cyclohexanone cyanohydrin
?
-
-
-
?
DL-mandelonitrile
benzaldehyde + HCN
-
-
-
?
ferrocenyl aldehyde + HCN
ferrocenyl-cyanohydrin
-
-
-
?
furan-3-carbaldehyde + HCN
(2S)-hydroxy(furan-3-yl)ethanenitrile
-
92% enantiomeric excess
-
?
HCN + (2E)-oct-2-enal
(2S,3E)-2-hydroxynon-3-enenitrile
-
-
-
?
HCN + (benzyloxy)acetaldehyde
3-(benzyloxy)-(2S)-2-hydroxy-propanenitrile + 3-(benzyloxy)-(2R)-2-hydroxy-propanenitrile
-
-
50% 3-(benzyloxy)-(2S)-2-hydroxy-propanenitrile and 50% 3-(benzyloxy)-(2R)-2-hydroxy-propanenitrile
?
HCN + (E)-2-butenal
(3E)-2-hydroxypent-3-enenitrile
-
-
-
?
HCN + 1,1'-diformylferrocene
(R,R)-1,1-bis(cyanohydroxymethyl)ferrocene
-
-
-
?
HCN + 2,2-dimethylpropanal
2-hydroxy-3,3-dimethylbutyronitrile
-
-
-
?
HCN + 2-allyloxybutanal
3-allyloxy-2-hydroxypentanenitrile
-
-
-
?
HCN + 2-allyloxyheptanal
(2R,3RS)-3-allyloxy-2-hydroxyoctanenitrile
-
-
-
?
HCN + 2-allyloxyhexanal
(2R,3RS)-3-allyloxy-2-hydroxyheptanenitrile
-
-
-
?
HCN + 2-allyloxypentanal
(2R,3RS)-3-allyloxy-2-hydroxyhexanenitrile
-
-
-
?
HCN + 2-allyloxypropanal
3-allyloxy-2-hydroxybutanenitrile
-
-
-
?
HCN + 2-benzyloxypropanal
3-benzyloxy-2-hydroxybutanenitrile
-
-
-
?
HCN + 2-chlorobenzaldehyde
(2-chlorophenyl)(hydroxy)acetonitrile
-
-
-
?
HCN + 2-hexenal
2-hydroxyhept-3-enenitrile
-
-
-
?
HCN + 2-methoxymethoxypropanal
3-methoxymethoxy-2-hydroxybutanenitrile
-
-
-
?
HCN + 2-methylallyloxyacetaldehyde
3-(2-methylallyloxy)-2-hydroxypropionitrile
-
-
-
?
HCN + 2-methyldihydrofuran
3-hydroxy-2-methyltetrahydrofuran-3-carbonitrile
-
analysis of diastereomeric distribution of the products, depending on different reaction conditions such as pH, reaction time, and solvent properties
-
?
HCN + 2-methyldihydrothiophen-3(2H)-one
3-hydroxy-2-methyltetrahydrothiophen-3-carbonitrile
-
analysis of diastereomeric distribution of the products, depending on different reaction conditions such as pH, reaction time, and solvent properties
-
?
HCN + 2-naphthaldehyde
(2S)-2-hydroxynaphthalen-2-yl-acetonitrile + (2R)-2-hydroxynaphthalen-2-yl-acetonitrile
-
-
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
-
-
84.3% (2S)-2-hydroxy-3-naphthalen-1-yl-propionitrile and 15.6% (2R)-2-hydroxy-3-naphthalen-1-yl-propionitrile
?
HCN + 2-propenal
2-hydroxybut-3-enenitrile
-
-
-
?
HCN + 3-furaldehyde
(2R)-3-furyl(hydroxy)acetonitrile
-
-
-
?
HCN + 3-furylcarbaldehyde
hydroxy(fur-3yl)acetonitrile
-
-
-
?
HCN + 3-phenoxybenzaldehyde
(2S)-hydroxy(3-phenoxyphenyl)acetonitrile
-
-
-
?
HCN + 3-phenoxypropanal
(2S)-2-hydroxy-4-phenoxybutanenitrile + (2S)-2-hydroxy-4-phenoxybutanenitrile
-
-
95.8% (2S)-2-hydroxy-4-phenoxybutanenitrile and 4.2% (2R)-2-hydroxy-4-phenoxybutanenitrile
?
HCN + 3-phenylpropionaldehyde
(2S)-2-hydroxy-4-phenylbutanenitrile
HCN + 4-methoxybenzaldehyde
(4-methoxyphenyl) (hydroxy)acetonitrile
-
-
-
?
HCN + acrolein
(2S)-2-hydroxybut-3-enenitrile
HCN + allyloxy-2-hydroxypropionitrile
3-allyloxy-2-hydroxypropionitrile
-
-
-
?
HCN + benzaldehyde
(R)-mandelonitrile
HCN + benzaldehyde
(S)-mandelonitrile
HCN + benzene-1,2,4-tricarbaldehyde
?
-
-
-
?
HCN + benzyloxyacetaldehyde
3-benzyloxy-2-hydroxypropionitrile
-
-
-
?
HCN + cyclohexanecarbaldehyde
(2R)-cyclohexyl(hydroxy)acetonitrile
-
-
-
?
HCN + decanal
(S)-2-hydroxyundecanenitrile
-
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
-
-
?
HCN + dodecanal
(S)-2-hydroxytridecanenitrile
-
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
-
-
?
HCN + ferrocene aldehyde
?
-
-
-
?
HCN + formylferrocene
(R)-(cyanohydroxymethyl)ferrocene
-
-
-
?
HCN + furaldehyde
(2R)-furan-2-yl(hydroxy)ethanenitrile
-
enzyme encapsulated in sol-gel matrix
-
-
?
HCN + hexanal
(S)-2-hydroxyoctanenitrile
-
enzyme encapsulated in sol-gel matrix
-
-
?
HCN + isobutyraldehyde
2-hydroxy-3-methylbutyronitrile
-
-
-
?
HCN + m-phenoxybenzaldehyde
(S)-hydroxy-(3-phenoxy-phenyl)acetonitrile
-
enzyme encapsulated in sol-gel matrix
-
-
?
HCN + methoxymethoxyacetaldehyde
2-hydroxy-3-methoxymethoxypropionitrile
-
-
-
?
HCN + methyl isopropyl ketone
(S)-2-hydroxy-2,3-dimethylbutanenitrile
-
enzyme encapsulated in sol-gel matrix
-
-
?
HCN + pentanal
2-hydroxyhexanenitrile
-
-
-
?
HCN + phenylacetaldehyde
(2R)-2-hydroxy-3-phenylpropanenitrile
-
-
-
?
HCN + propanal
2-hydroxybutanenitrile
-
-
-
?
HCN + rac-2-methyl-3-phenylpropionaldehyde
(2S,3R)-2-hydroxy-3-methyl-4-phenylbutyronitrile
-
-
wild-type and mutant enzymes Y128Y, W128L, W128C, W128A are (S)-selective
-
?
HCN + rac-2-phenylbutyraldehyde
2-hydroxy-3-phenylpentanenitrile
-
-
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
-
-
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
-
-
wild-type and mutant enzymes Y128Y, W128L, W128C, W128A are (S)-selective
-
?
HCN + tetrahydro-2H-3-pyranone
(3R)-3-hydroxytetrahydro-2H-pyran-3-carbonitrile
-
-
enantiomeric excess at pH 4.75 is 48.3%
?
HCN + tetrahydro-3-furanone
(3R)-3-hydroxytetrahydrofuran-3-carbonitrile
-
-
81% enantiomeric excess
?
HCN + thiophen-2-carbaldehyde
hydroxy(thien-2-yl)acetonitrile
-
-
-
?
HCN + thiophen-3-carbaldehyde
hydroxy(thien-3-yl)acetonitrile
-
-
-
?
HCN + undecanal
(S)-2-hydroxydodecanenitrile
-
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
-
-
?
hexanal cyanohydrin
hexanal + HCN
Isobutyraldehyde + cyanide
2-Hydroxy-3-methylbutyronitrile
-
-
-
-
?
lactonitrile
?
poor substrate
-
-
?
m-phenoxybenzaldehyde cyanohydrin
m-phenoxybenzaldehyde + cyanide
2-phenoxybenzaldehyde cyanohydrin is converted with lower activity than (S)-mandelonitrile and cyclohexanone cyanohydrile
-
-
?
m-phenoxybenzaldehyde cyanohydrin
m-phenoxybenzaldehyde + HCN
mandelonitrile
benzaldehyde + HCN
mandelonitrile
cyanide + benzaldehyde
-
-
-
?
mandelonitrile
HCN + benzaldehyde
n-Butyraldehyde + cyanide
(S)-2-Hydroxyvaleronitrile
-
-
-
?
nitromethane + benzaldehyde
(S)-2-nitro-1-phenylethanol
-
-
-
-
r
p-hydroxymandelonitrile
?
phydroxymandelonitrile is converted with lower activity than (S)-mandelonitrile and cyclohexanone cyanohydrile
-
-
?
propionaldehyde cyanohydrin
propionaldehyde + cyanide
poor substrate
-
-
?
rac-2-nitro-1-phenylethanol
nitromethane + benzaldehyde
-
-
-
?
rac-mandelonitrile
benzaldehyde + HCN
-
-
-
?
rac-mandelonitrile
HCN + benzaldehyde
-
-
-
?
thiophene-2-carbaldehyde + HCN
(2S)-hydroxy(thiophen-2-yl)ethanenitrile
-
96% enantiomeric excess
-
?
thiophene-3-carbaldehyde + HCN
(2S)-hydroxy(thiophen-3-yl)ethanenitrile
-
98% enantiomeric excess
-
?
additional information
?
-
(2S)-2-hydroxy-2-methylbutanenitrile

cyanide + butan-2-one
-
-
-
?
(2S)-2-hydroxy-2-methylbutanenitrile
cyanide + butan-2-one
the liberation of HCN serves as a defense mechanism against herbivores and microbial attack in plants
-
-
?
(S)-mandelonitrile

benzaldehyde + HCN
-
enantiomeric excess: > 99%, yield: 90%
-
-
r
(S)-mandelonitrile
benzaldehyde + HCN
-
-
-
-
?
(S)-mandelonitrile

cyanide + benzaldehyde
-
-
-
r
(S)-mandelonitrile
cyanide + benzaldehyde
-
-
-
-
?
(S)-mandelonitrile
cyanide + benzaldehyde
-
-
-
-
r
(S)-mandelonitrile
cyanide + benzaldehyde
-
-
-
?
(S)-mandelonitrile
cyanide + benzaldehyde
-
-
-
r
(S)-mandelonitrile
cyanide + benzaldehyde
binding mode of the chiral substrate is identical to that observed for the biological substrate 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
-
-
?
(S)-mandelonitrile
cyanide + benzaldehyde
enzyme kinetics in both directions is studied on a model system with mandelonitrile, benzaldehyde, and HCN using two different methods: initial rate measurements and progress curve analysis. Ordered Uni bi mechanism with the formation of a dead-end complex of enzyme, (S)-mandelonitrile and HCN. HCN is the first product released from the enzyme followed by benzaldehyde while in the synthesis reaction, benzaldehyde is the first substrate bond to the enzyme followed by HCN
-
-
r
(S)-mandelonitrile
cyanide + benzaldehyde
the enzymatic reversible conversion of (S)-mandelonitrile to HCN and benzaldehyde can be adequately described by a three-step, reversible-ordered UniĆ¢ĀĀBi reaction scheme
-
-
r
(S)-mandelonitrile
cyanide + benzaldehyde
the enzyme is a member of the alpha/beta hydrolase fold protein family, containing a catalytic triad with C-C cleaving and ligating activity
-
-
r
(S)-mandelonitrile
cyanide + benzaldehyde
-
-
-
-
?
(S)-mandelonitrile
cyanide + benzaldehyde
-
-
-
r
(S)-mandelonitrile
cyanide + benzaldehyde
-
-
-
-
r
(S)-mandelonitrile
cyanide + benzaldehyde
-
-
-
?
(S)-mandelonitrile
cyanide + benzaldehyde
-
-
-
-
?
(S)-mandelonitrile
cyanide + benzaldehyde
-
-
-
r
(S)-mandelonitrile
cyanide + benzaldehyde
high selectivity towards the (S)-enentiomer
-
-
?
(S)-mandelonitrile

HCN + benzaldehyde
-
-
-
-
?
(S)-mandelonitrile
HCN + benzaldehyde
-
highly (S)-selective
-
?
(S)-mandelonitrile
HCN + benzaldehyde
-
-
-
-
?
2-furaldehyde cyanohydrin

2-furaldehyde + HCN
-
aqua gel, 30 min, conversion ratio: 89%, enantiomeric excess: 94%
-
-
r
2-furaldehyde cyanohydrin
2-furaldehyde + HCN
-
free enzyme, 30 min, conversion ratio: 89%,enantiomeric excess: 94%
-
-
r
2-hydroxy-2-methylpropanenitrile

acetone + HCN
-
-
-
?
2-hydroxy-2-methylpropanenitrile
acetone + HCN
-
-
-
-
r
2-hydroxy-2-methylpropanenitrile
acetone + HCN
-
release of HCN serves as a defense against herbivores and microbial attack of the plant
-
?
2-hydroxy-2-methylpropanenitrile
acetone + HCN
-
-
-
-
?
2-hydroxy-2-methylpropanenitrile
acetone + HCN
-
-
-
?
2-hydroxy-2-methylpropanenitrile
acetone + HCN
acetone cyanohydrin spontaneously decomposes to acetone and cyanide at pH above 5.0 or temperatures above 35 C
-
-
?
2-hydroxy-2-methylpropanenitrile

cyanide + acetone
-
-
-
?
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
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
-
-
?
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
-
-
-
-
?
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
-
-
-
?
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
-
-
-
-
?
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
-
-
-
?
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
i.e. acetone cyanohydrin
-
-
?
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
-
i.e. acetone cyanohydrin
-
-
?
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
i.e. acetone cyanohydrin, catalyzes the decomposition of the achiral alpha-hydroxynitrile 2-hydroxy-2-methylpropanenitrile into HCN and acetone during cyanogenesis of damaged plants
-
-
?
2-hydroxy-2-methylpropanenitrile
cyanide + acetone
the liberation of HCN serves as a defense mechanism against herbivores and microbial attack in plants
-
-
?
2-hydroxy-2-methylpropanenitrile

HCN + acetone
-
-
-
?
2-hydroxy-2-methylpropanenitrile
HCN + acetone
-
liberation of HCN by degradation of acetone cyanohydrin is considerably faster than the consumption of HCN by the formation of (S)-mandelonitrile
-
?
2-hydroxy-2-methylpropanenitrile
HCN + acetone
-
release of HCN serves as a defense against herbivores and microbial attack of the plant
-
?
2-hydroxy-2-methylpropanenitrile
HCN + acetone
-
-
-
?
2-nitro-1-phenylethanol

?
-
-
-
-
?
2-nitro-1-phenylethanol
?
-
very low turnover number
-
-
?
Acetone cyanhydrin

Cyanide + acetone
-
-
-
?
Acetone cyanhydrin
Cyanide + acetone
-
-
-
?
Acetone cyanhydrin
Cyanide + acetone
-
-
-
?
acetone cyanhydrin

HCN + acetone
-
-
-
?
acetone cyanhydrin
HCN + acetone
-
S-specific
-
?
acetone cyanohydrin

cyanide + acetone
-
-
-
-
?
acetone cyanohydrin
cyanide + acetone
-
-
-
?
cyanide + (2E)-hex-2-enal

(2S,3E)-2-hydroxyhept-3-enenitrile
-
95% enantiomeric excess with crude enzyme preparation
-
?
cyanide + (2E)-hex-2-enal
(2S,3E)-2-hydroxyhept-3-enenitrile
-
97% enantiomeric excess
-
?
cyanide + (2E)-hex-2-enal
(2S,3E)-2-hydroxyhept-3-enenitrile
-
wild-type enzyme: 97% enantiomeric excess, 58% conversion rate
-
?
cyanide + 1-naphthalene carboxaldehyde

?
-
-
-
?
cyanide + 1-naphthalene carboxaldehyde
?
-
-
-
?
cyanide + 2,2-dimethylpropanal

(2S)-2-hydroxy-3,3-dimethylbutanenitrile
-
67% enantiomeric excess
-
?
cyanide + 2,2-dimethylpropanal
(2S)-2-hydroxy-3,3-dimethylbutanenitrile
-
94% enantiomeric excess
-
?
cyanide + 2-methylpropanal

(2S)-2-hydroxy-3-methylbutanenitrile
-
81% enantiomeric excess
-
?
cyanide + 2-methylpropanal
(2S)-2-hydroxy-3-methylbutanenitrile
-
95% enantiomeric excess
-
?
cyanide + 2-thiophene carboxaldehyde

?
-
-
-
?
cyanide + 2-thiophene carboxaldehyde
?
-
-
-
?
cyanide + 3-phenylpropanal

(2S)-2-hydroxy-4-phenylbutanenitrile
-
-
-
-
?
cyanide + 3-phenylpropanal
(2S)-2-hydroxy-4-phenylbutanenitrile
-
93% enantiomeric excess
-
?
cyanide + 4-biphenyl carboxaldehyde

?
-
-
-
?
cyanide + 4-biphenyl carboxaldehyde
?
-
-
-
?
cyanide + benzaldehyde

(S)-mandelonitrile
-
-
-
-
?
cyanide + benzaldehyde
(S)-mandelonitrile
-
-
-
r
cyanide + benzaldehyde
(S)-mandelonitrile
-
68% yield, 54% enantiomeric excess
-
?
cyanide + benzaldehyde
(S)-mandelonitrile
-
-
-
-
?
cyanide + benzaldehyde
(S)-mandelonitrile
-
-
-
-
r
cyanide + benzaldehyde
(S)-mandelonitrile
-
94% enantiomeric excess
-
?
cyanide + benzaldehyde
(S)-mandelonitrile
-
-
-
-
?
cyanide + benzaldehyde
(S)-mandelonitrile
-
-
-
r
cyanide + benzaldehyde
(S)-mandelonitrile
-
-
-
-
r
cyanide + benzaldehyde
(S)-mandelonitrile
-
-
-
r
cyanide + benzaldehyde
(S)-mandelonitrile
-
98% enantiomeric excess
-
?
cyanide + benzaldehyde
(S)-mandelonitrile
-
wild-type enzyme: 99% enantiomeric excess, 97% conversion rate
-
?
cyanide + benzaldehyde
(S)-mandelonitrile
-
-
low enantioselectivity with 20% ee (S)
-
r
cyanide + benzaldehyde
(S)-mandelonitrile
concentrations of benzaldehyde higher than 1 M result in decreased enantioselectivity due to nonenzymatic formation of racemic mandelonitrile due to an excess of benzaldehyde and cyanide
-
-
?
cyanide + benzaldehyde
(S)-mandelonitrile
the (S)-cyanohydrin is formed with more than 99.5% enantiomeric excess
-
-
r
cyanide + prop-2-enal

(2S)-2-hydroxybut-3-enenitrile
-
94% enantiomeric excess with crude enzyme preparation
-
?
cyanide + prop-2-enal
(2S)-2-hydroxybut-3-enenitrile
-
47% enantiomeric excess
-
?
cyanide + propanal

(2S)-2-hydroxybutanenitrile
-
-
-
-
?
cyanide + propanal
(2S)-2-hydroxybutanenitrile
-
91% enantiomeric excess
-
?
HCN + 3-phenylpropionaldehyde

(2S)-2-hydroxy-4-phenylbutanenitrile
-
-
89% enantiomeric excess
?
HCN + 3-phenylpropionaldehyde
(2S)-2-hydroxy-4-phenylbutanenitrile
-
-
67% enantiomeric excess
?
HCN + acrolein

(2S)-2-hydroxybut-3-enenitrile
-
-
92% enantiomeric ecxess
?
HCN + acrolein
(2S)-2-hydroxybut-3-enenitrile
-
-
59% enantiomeric excess
?
HCN + benzaldehyde

(R)-mandelonitrile
-
-
-
?
HCN + benzaldehyde
(R)-mandelonitrile
-
-
-
?
HCN + benzaldehyde

(S)-mandelonitrile
-
-
99% enantiomeric excess
?
HCN + benzaldehyde
(S)-mandelonitrile
-
enzyme encapsulated in sol-gel matrix
-
-
?
HCN + benzaldehyde
(S)-mandelonitrile
-
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
-
-
?
HCN + benzaldehyde
(S)-mandelonitrile
-
-
99% enantiomeric excess
?
hexanal cyanohydrin

hexanal + HCN
-
aqua gel, 2 h, conversion ratio: 92%, enantiomeric excess: 94%
-
-
r
hexanal cyanohydrin
hexanal + HCN
-
free enzyme, 4 h, conversion ratio: 91%,enantiomeric excess: 94%
-
-
r
m-phenoxybenzaldehyde cyanohydrin

m-phenoxybenzaldehyde + HCN
-
aqua gel, 72 h, conversion ratio: 92%, enantiomeric excess: 98%
-
-
r
m-phenoxybenzaldehyde cyanohydrin
m-phenoxybenzaldehyde + HCN
-
free enzyme, 72 h, conversion ratio: 45%,enantiomeric excess: 82%
-
-
r
mandelonitrile

benzaldehyde + HCN
-
aqua gel, 0.5 h, conversion ratio: 97%, enantiomeric excess: 99%
-
-
r
mandelonitrile
benzaldehyde + HCN
-
CLEA, 72 h, conversion ratio: 55%, enantiomeric excess: 67%
-
-
r
mandelonitrile
benzaldehyde + HCN
-
free enzyme, 4 h, conversion ratio: 97%,enantiomeric excess: 97%
-
-
r
mandelonitrile

HCN + benzaldehyde
-
racemic
-
?
mandelonitrile
HCN + benzaldehyde
racemic
-
?
mandelonitrile
HCN + benzaldehyde
-
-
-
?
additional information

?
-
-
acetylferrocene and 1,1'-diacetylferrocene are not transformed with this enzyme
-
-
?
additional information
?
-
-
acetylferrocene and 1,1'-diacetylferrocene are not transformed with this enzyme
-
?
additional information
?
-
-
the enantiomeric excess of the product is optimal at pH 5.4 and at HCN concentration between 200 mM and 400 mM and clearly decreases at concentrations greater than 1.5 M. When the temperature decreases from 25ưC to -5ưC, the enantiomeric excess increases from 88% to 95%
-
-
?
additional information
?
-
-
the enantiomeric excess of the product is optimal at pH 5.4 and at HCN concentration between 200 mM and 400 mM and clearly decreases at concentrations greater than 1.5 M. When the temperature decreases from 25ưC to -5ưC, the enantiomeric excess increases from 88% to 95%
-
?
additional information
?
-
(3E)-2-hydroxy-4-phenylbut-3-enenitrile is not sufficently accepted by the enzyme in crude enzyme preparation
-
-
?
additional information
?
-
modeling of the complexes of the enzyme with its natural substrate acetone cyanohydrin as well as with the chiral compounds mandelonitrile and 2,3-dimethyl-2-hydroxybutyronitril. Enzymatic mechanism involves catalytic triad Ser80, His235, and Asp207 as a genertal acid/base
-
-
?
additional information
?
-
-
modeling of the complexes of the enzyme with its natural substrate acetone cyanohydrin as well as with the chiral compounds mandelonitrile and 2,3-dimethyl-2-hydroxybutyronitril. Enzymatic mechanism involves catalytic triad Ser80, His235, and Asp207 as a genertal acid/base
-
-
?
additional information
?
-
-
theoretical investigation of the catalytic mechanism
-
-
?
additional information
?
-
theoretical investigation of the catalytic mechanism
-
-
?
additional information
?
-
-
the enzyme catalyzes asymmetric cyanohydrin and Henry reactions. (R)-2-nitro-1-phenylethanol is not a substrate or HNL
-
-
?
additional information
?
-
-
the enzyme has low activity in performing Henry reactions
-
-
?
additional information
?
-
on the basis of extensive QM/MM MD and RAMD MD simulations, the catalytic mechanism of the enzyme and its substrate delivery and product (HCN) release are explored. The catalytic reaction approximately follows a two-stage mechanism. The first stage involves two fast processes including the proton abstraction of the substrate through a double-proton transfer and the C-CN bond cleavage, while the second stage concerns HCN formation and is rate-determining
-
-
?
additional information
?
-
-
When the temperature decreases from 25ưC to -5ưC, the enantiomeric excess increases from 67% to 74%
-
-
?
additional information
?
-
-
When the temperature decreases from 25ưC to -5ưC, the enantiomeric excess increases from 67% to 74%
-
?
additional information
?
-
the enzyme catalyzes enantioselective addition of HCN to aromatic, heteroaromatic and aliphatic aldehydes and ketones forming (S)-aldehyde cyanohydrins or (S)-ketone cyanohydrins
-
-
?
additional information
?
-
wild-type enzyme shows very low activity with 4-hydroxymandelonitrile, activity of mutant enzyme W128A is increased 450fold compared to wild-type value (Km-value for mutant enzyme W128A is 0.625 mM)
-
-
?
additional information
?
-
-
wild-type enzyme shows very low activity with 4-hydroxymandelonitrile, activity of mutant enzyme W128A is increased 450fold compared to wild-type value (Km-value for mutant enzyme W128A is 0.625 mM)
-
-
?
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0.28 - 1.49
(R)-mandelonitrile
2.6
(S)-2-nitro-1-phenylethanol
0.34 - 30
(S)-mandelonitrile
0.2 - 1.4
1-naphthalene carboxaldehyde
5.2
2,4-dimethylbenzaldehyde
pH 6.0, 25ưC
67 - 150
2-hydroxy-2-methylpropanenitrile
0.8
2-Methyl-2-hydroxybutyronitrile
-
-
21.7
2-Methylbenzaldehyde
pH 6.0, 25ưC
0.4 - 7.1
2-nitro-1-phenylethanol
34.1 - 47.5
2-thiophene carboxaldehyde
161.5
3,3-dimethyl-2-butanone
-
pH 5.4, 40ưC
9.8
3-Methoxybenzaldehyde
pH 6.0, 25ưC
14.4
3-methylbenzaldehyde
pH 6.0, 25ưC
25.4
4-biphenyl carboxaldehyde
pH 4.2, 22ưC
0.7 - 174
acetone cyanohydrin
61.5
acetyltrimethylsilane
-
pH 5.4, 40ưC
15.7
piperonal
pH 6.0, 25ưC
0.4 - 7.1
rac-2-nitro-1-phenylethanol
0.6 - 9.4
rac-mandelonitrile
additional information
additional information
-
0.28
(R)-mandelonitrile

pH 4.23, 25ưC, mutant enzyme H103C
0.61
(R)-mandelonitrile
pH 4.23, 25ưC, mutant enzyme H103C/N156D
1.49
(R)-mandelonitrile
pH 4.23, 25ưC, mutant enzyme H103C/N156G
2.6
(S)-2-nitro-1-phenylethanol

-
in 50 mM phosphate buffer pH 6.0, at 25ưC
2.6
(S)-2-nitro-1-phenylethanol
-
in 50 mM phosphate buffer pH 6.0, at 22ưC
0.34
(S)-mandelonitrile

pH 4.23, 25ưC, mutant enzyme H103C
0.47
(S)-mandelonitrile
pH 4.23, 25ưC, mutant enzyme H103C/N156D
0.49
(S)-mandelonitrile
pH 4.23, 25ưC, mutant enzyme H103C/N156G
1.2
(S)-mandelonitrile
-
in 50 mM citrate buffer (pH 5.0), temperature not specified in the publication
1.4
(S)-mandelonitrile
-
in 50 mM citrate buffer (pH 5.0), temperature not specified in the publication
1.86
(S)-mandelonitrile
mutant enzyme H103M, in 100 mM citrate buffer pH above 6.0, temperature not specified in the publication
2.5 - 5
(S)-mandelonitrile
mutant enzyme H103L, in 100 mM citrate buffer pH above 6.0, temperature not specified in the publication
4.1
(S)-mandelonitrile
pH 7.5
4.1
(S)-mandelonitrile
citrate buffer (50 mM, pH 4.0), at 25ưC
4.5
(S)-mandelonitrile
pH 5.2, 23ưC, mutant enzyme W128A
5.17
(S)-mandelonitrile
wild type enzyme, in 100 mM citrate buffer pH above 6.0, temperature not specified in the publication
5.54
(S)-mandelonitrile
mutant enzyme K176P/K199P/K224P, in 100 mM citrate buffer pH above 6.0, temperature not specified in the publication
6.98
(S)-mandelonitrile
mutant enzyme K176P, in 100 mM citrate buffer pH above 6.0, temperature not specified in the publication
30
(S)-mandelonitrile
pH 5.2, 23ưC, wild-type enzyme
0.2
1-naphthalene carboxaldehyde

pH 4.2, 22ưC
1.4
1-naphthalene carboxaldehyde
pH 4.2, 22ưC
67
2-hydroxy-2-methylpropanenitrile

pH 5.2, 23ưC, wild-type enzyme
95
2-hydroxy-2-methylpropanenitrile
mutant enzyme H112A
101
2-hydroxy-2-methylpropanenitrile
recombinant enzyme
120
2-hydroxy-2-methylpropanenitrile
wild-type enzyme
120
2-hydroxy-2-methylpropanenitrile
mutant enzyme D130A
120
2-hydroxy-2-methylpropanenitrile
mutant enzyme D95A
125
2-hydroxy-2-methylpropanenitrile
mutant enzyme H5A
130
2-hydroxy-2-methylpropanenitrile
mutant enzyme H10A
150
2-hydroxy-2-methylpropanenitrile
pH 5.2, 23ưC, mutant enzyme W128A
0.4
2-nitro-1-phenylethanol

mutant enzyme F125T/L146M, pH and temperature not specified in the publication
0.7
2-nitro-1-phenylethanol
mutant enzyme F125T/Y133F, pH and temperature not specified in the publication
1.4
2-nitro-1-phenylethanol
mutant enzyme V106F, pH and temperature not specified in the publication
1.6
2-nitro-1-phenylethanol
mutant enzyme V106F/L121Y, pH and temperature not specified in the publication
1.8
2-nitro-1-phenylethanol
mutant enzyme V106F/F125T, pH and temperature not specified in the publication
5
2-nitro-1-phenylethanol
mutant enzyme C81L, pH and temperature not specified in the publication
5
2-nitro-1-phenylethanol
mutant enzyme F125T, pH and temperature not specified in the publication
5
2-nitro-1-phenylethanol
mutant enzyme L121Y, pH and temperature not specified in the publication
5
2-nitro-1-phenylethanol
mutant enzyme L121Y/F125T/L146M, pH and temperature not specified in the publication
5
2-nitro-1-phenylethanol
mutant enzyme L121Y/F125T/Y133F, pH and temperature not specified in the publication
5
2-nitro-1-phenylethanol
mutant enzyme L121Y/L146M, pH and temperature not specified in the publication
5
2-nitro-1-phenylethanol
mutant enzyme L146M, pH and temperature not specified in the publication
5
2-nitro-1-phenylethanol
mutant enzyme V106F/L121Y/F125T, pH and temperature not specified in the publication
5
2-nitro-1-phenylethanol
mutant enzyme V106F/L146M, pH and temperature not specified in the publication
6.1
2-nitro-1-phenylethanol
wild type enzyme, pH and temperature not specified in the publication
7.1
2-nitro-1-phenylethanol
mutant enzyme Y133F, pH and temperature not specified in the publication
34.1
2-thiophene carboxaldehyde

pH 4.2, 22ưC
47.5
2-thiophene carboxaldehyde
pH 4.2, 22ưC
0.7
acetone cyanohydrin

-
-
4
acetone cyanohydrin
-
-
115
acetone cyanohydrin
pH 5.4
169
acetone cyanohydrin
-
mutant enzyme C81A
174
acetone cyanohydrin
-
wild-type enzyme
2 - 3
benzaldehyde

wild type enzyme, in 100 mM citrate buffer pH 5.0, temperature not specified in the publication
5.5
benzaldehyde
pH 6.0, 25ưC
5.9
benzaldehyde
citrate buffer (50 mM, pH 4.0), at 25ưC
12.3
benzaldehyde
mutant enzyme H103Y, in 100 mM citrate buffer pH 5.0, temperature not specified in the publication
13.4
benzaldehyde
mutant enzyme H103L, in 100 mM citrate buffer pH 5.0, temperature not specified in the publication
21.6
benzaldehyde
mutant enzyme K176P, in 100 mM citrate buffer pH 5.0, temperature not specified in the publication
27
benzaldehyde
mutant enzyme K176P/K199P/K224P, in 100 mM citrate buffer pH 5.0, temperature not specified in the publication
27.9
benzaldehyde
mutant enzyme H103M, in 100 mM citrate buffer pH 5.0, temperature not specified in the publication
179
cyanide

pH 7.5
179
cyanide
citrate buffer (50 mM, pH 4.0), at 25ưC
0.6
mandelonitrile

mutant enzyme L152F, pH and temperature not specified in the publication
0.7
mandelonitrile
mutant enzyme I209G, pH and temperature not specified in the publication
0.8
mandelonitrile
mutant enzyme I209A, pH and temperature not specified in the publication
1.1
mandelonitrile
-
pH 5.4, 25ưC, mutant enzyme G113S
1.4
mandelonitrile
-
pH 5.4, 25ưC, wild-type enzyme
1.4
mandelonitrile
mutant enzyme V106F/L121Y, pH and temperature not specified in the publication
1.5
mandelonitrile
mutant enzyme F125T/L146M, pH and temperature not specified in the publication
2
mandelonitrile
mutant enzyme F125T, pH and temperature not specified in the publication
2
mandelonitrile
mutant enzyme V106F/L121Y/F125T, pH and temperature not specified in the publication
2.1
mandelonitrile
mutant enzyme F125T/Y133F, pH and temperature not specified in the publication
2.7
mandelonitrile
mutant enzyme L121Y, pH and temperature not specified in the publication
3.1
mandelonitrile
mutant enzyme L121Y/F125T, pH and temperature not specified in the publication
3.1
mandelonitrile
mutant enzyme Y133F, pH and temperature not specified in the publication
3.3
mandelonitrile
wild type enzyme, pH and temperature not specified in the publication
3.6
mandelonitrile
mutant enzyme L121Y/F125T/L146M, pH and temperature not specified in the publication
3.7
mandelonitrile
mutant enzyme L146M, pH and temperature not specified in the publication
5.3
mandelonitrile
mutant enzyme V106F, pH and temperature not specified in the publication
6.7
mandelonitrile
mutant enzyme L121Y/L146M, pH and temperature not specified in the publication
8.6
mandelonitrile
mutant enzyme F210I, pH and temperature not specified in the publication
8.6
mandelonitrile
mutant enzyme L148F, pH and temperature not specified in the publication
9.4
mandelonitrile
mutant enzyme C81L, pH and temperature not specified in the publication
0.4
rac-2-nitro-1-phenylethanol

pH 5.0, temperature not specified in the publication, mutant enzyme F125T/L146M
0.7
rac-2-nitro-1-phenylethanol
pH 5.0, temperature not specified in the publication, mutant enzyme F125T/Y133F
1.4
rac-2-nitro-1-phenylethanol
pH 5.0, temperature not specified in the publication, mutant enzyme V106F
1.6
rac-2-nitro-1-phenylethanol
pH 5.0, temperature not specified in the publication, mutant enzyme V106F/L121Y
1.8
rac-2-nitro-1-phenylethanol
pH 5.0, temperature not specified in the publication, mutant enzyme V106F/F125T
6.1
rac-2-nitro-1-phenylethanol
pH 5.0, temperature not specified in the publication, wild-type enzyme
7.1
rac-2-nitro-1-phenylethanol
pH 5.0, temperature not specified in the publication, mutant enzyme Y133F
0.6
rac-mandelonitrile

pH 5.0, temperature not specified in the publication, mutant enzyme L152F
0.7
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme I209G
0.8
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme I209A
1.4
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme V106F/L121Y
1.5
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme F125T/L146M
1.5
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121F
2
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme F125T
2
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme V106F/L121Y/F125T
2.1
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme F125T/Y133F
2.7
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121T
2.7
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121Y
2.8
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121A
3.1
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121Y/F125T
3.1
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme Y133F
3.3
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, wild-type enzyme
3.6
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121Y/F125T/L146M
3.7
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121V
3.7
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L146M
4
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121M
4.9
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121I
5.3
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme V106F
5.6
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121W
5.7
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121Q
6.6
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121S
6.7
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121Y/L146M
8
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121H
8.1
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121C
8.6
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme F210I
8.6
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L148F
9.4
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme C81L
additional information
additional information

-
-
-
additional information
additional information
a kinetic investigation based on the rate curve method
-
additional information
additional information
-
a kinetic investigation based on the rate curve method
-
additional information
additional information
wild-type enzyme shows very low activity with 4-hydroxymandelonitrile, activity of mutant enzyme W128A is increased 450fold compared to wild-type value (Km-value for mutant enzyme W128A is 0.625 mM)
-
additional information
additional information
-
wild-type enzyme shows very low activity with 4-hydroxymandelonitrile, activity of mutant enzyme W128A is increased 450fold compared to wild-type value (Km-value for mutant enzyme W128A is 0.625 mM)
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
7.98 - 12.7
(R)-mandelonitrile
1.83 - 122
(S)-mandelonitrile
6 - 23.5
1-naphthalene carboxaldehyde
18.5
2,4-dimethylbenzaldehyde
pH 6.0, 25ưC
53.6
2-Methylbenzaldehyde
pH 6.0, 25ưC
0.1 - 0.6
2-nitro-1-phenylethanol
31.5 - 100
2-thiophene carboxaldehyde
28.1
3-Methoxybenzaldehyde
pH 6.0, 25ưC
49.2
3-methylbenzaldehyde
pH 6.0, 25ưC
9.2
4-biphenyl carboxaldehyde
pH 4.2, 22ưC
91.4
piperonal
pH 6.0, 25ưC
0.1 - 0.6
rac-2-nitro-1-phenylethanol
3 - 106
rac-mandelonitrile
7.98
(R)-mandelonitrile

pH 4.23, 25ưC, mutant enzyme H103C
9.27
(R)-mandelonitrile
pH 4.23, 25ưC, mutant enzyme H103C/N156D
12.7
(R)-mandelonitrile
pH 4.23, 25ưC, mutant enzyme H103C/N156G
1.83
(S)-mandelonitrile

-
in 50 mM citrate buffer (pH 5.0), temperature not specified in the publication
21.5
(S)-mandelonitrile
mutant enzyme H103L, in 100 mM citrate buffer pH above 6.0, temperature not specified in the publication
21.67
(S)-mandelonitrile
-
in 50 mM citrate buffer (pH 5.0), temperature not specified in the publication
23.9
(S)-mandelonitrile
mutant enzyme H103M, in 100 mM citrate buffer pH above 6.0, temperature not specified in the publication
34.5
(S)-mandelonitrile
wild type enzyme, in 100 mM citrate buffer pH above 6.0, temperature not specified in the publication
39.7
(S)-mandelonitrile
mutant enzyme K176P/K199P/K224P, in 100 mM citrate buffer pH above 6.0, temperature not specified in the publication
41.8
(S)-mandelonitrile
mutant enzyme K176P, in 100 mM citrate buffer pH above 6.0, temperature not specified in the publication
52.9
(S)-mandelonitrile
pH 4.23, 25ưC, mutant enzyme H103C
88.1
(S)-mandelonitrile
pH 4.23, 25ưC, mutant enzyme H103C/N156D
122
(S)-mandelonitrile
pH 4.23, 25ưC, mutant enzyme H103C/N156G
6
1-naphthalene carboxaldehyde

pH 4.2, 22ưC
23.5
1-naphthalene carboxaldehyde
pH 4.2, 22ưC
0.1
2-nitro-1-phenylethanol

mutant enzyme F125T/L146M, pH and temperature not specified in the publication
0.1
2-nitro-1-phenylethanol
mutant enzyme L121Y/L146M, pH and temperature not specified in the publication
0.1
2-nitro-1-phenylethanol
mutant enzyme V106F, pH and temperature not specified in the publication
0.1
2-nitro-1-phenylethanol
mutant enzyme V106F/L121Y, pH and temperature not specified in the publication
0.12
2-nitro-1-phenylethanol
mutant enzyme F125T/Y133F, pH and temperature not specified in the publication
0.15
2-nitro-1-phenylethanol
wild type enzyme, pH and temperature not specified in the publication
0.2
2-nitro-1-phenylethanol
mutant enzyme C81L, pH and temperature not specified in the publication
0.2
2-nitro-1-phenylethanol
mutant enzyme V106F/F125T, pH and temperature not specified in the publication
0.2
2-nitro-1-phenylethanol
mutant enzyme V106F/L146M, pH and temperature not specified in the publication
0.3
2-nitro-1-phenylethanol
mutant enzyme Y133F, pH and temperature not specified in the publication
0.5
2-nitro-1-phenylethanol
mutant enzyme L121Y, pH and temperature not specified in the publication
0.5
2-nitro-1-phenylethanol
mutant enzyme L121Y/F125T/L146M, pH and temperature not specified in the publication
0.5
2-nitro-1-phenylethanol
mutant enzyme L121Y/F125T/Y133F, pH and temperature not specified in the publication
0.5
2-nitro-1-phenylethanol
mutant enzyme L146M, pH and temperature not specified in the publication
0.5
2-nitro-1-phenylethanol
mutant enzyme V106F/L121Y/F125T, pH and temperature not specified in the publication
0.6
2-nitro-1-phenylethanol
mutant enzyme F125T, pH and temperature not specified in the publication
31.5
2-thiophene carboxaldehyde

pH 4.2, 22ưC
100
2-thiophene carboxaldehyde
pH 4.2, 22ưC
26.6
benzaldehyde

pH 6.0, 25ưC
47.4
benzaldehyde
mutant enzyme H103Y, in 100 mM citrate buffer pH 5.0, temperature not specified in the publication
83.2
benzaldehyde
mutant enzyme K176P, in 100 mM citrate buffer pH 5.0, temperature not specified in the publication
90.4
benzaldehyde
mutant enzyme H103L, in 100 mM citrate buffer pH 5.0, temperature not specified in the publication
93.5
benzaldehyde
mutant enzyme K176P/K199P/K224P, in 100 mM citrate buffer pH 5.0, temperature not specified in the publication
96.1
benzaldehyde
mutant enzyme H103M, in 100 mM citrate buffer pH 5.0, temperature not specified in the publication
96.6
benzaldehyde
wild type enzyme, in 100 mM citrate buffer pH 5.0, temperature not specified in the publication
3
mandelonitrile

mutant enzyme I209G, pH and temperature not specified in the publication
7
mandelonitrile
mutant enzyme L152F, pH and temperature not specified in the publication
7
mandelonitrile
mutant enzyme V106F, pH and temperature not specified in the publication
17
mandelonitrile
mutant enzyme L148F, pH and temperature not specified in the publication
20
mandelonitrile
mutant enzyme L146M, pH and temperature not specified in the publication
21
mandelonitrile
mutant enzyme F210I, pH and temperature not specified in the publication
22
mandelonitrile
mutant enzyme Y133F, pH and temperature not specified in the publication
23
mandelonitrile
mutant enzyme I209A, pH and temperature not specified in the publication
25
mandelonitrile
wild type enzyme, pH and temperature not specified in the publication
32
mandelonitrile
mutant enzyme F125T/L146M, pH and temperature not specified in the publication
32
mandelonitrile
mutant enzyme F125T/Y133F, pH and temperature not specified in the publication
33
mandelonitrile
mutant enzyme C81L, pH and temperature not specified in the publication
43
mandelonitrile
mutant enzyme L121Y/F125T, pH and temperature not specified in the publication
45
mandelonitrile
mutant enzyme L121Y/F125T/L146M, pH and temperature not specified in the publication
55
mandelonitrile
mutant enzyme V106F/L121Y, pH and temperature not specified in the publication
66
mandelonitrile
mutant enzyme F125T, pH and temperature not specified in the publication
82
mandelonitrile
mutant enzyme V106F/L121Y/F125T, pH and temperature not specified in the publication
106
mandelonitrile
mutant enzyme L121Y, pH and temperature not specified in the publication
0.1
rac-2-nitro-1-phenylethanol

pH 5.0, temperature not specified in the publication, mutant enzyme F125T/L146M
0.1
rac-2-nitro-1-phenylethanol
pH 5.0, temperature not specified in the publication, mutant enzyme V106F
0.12
rac-2-nitro-1-phenylethanol
pH 5.0, temperature not specified in the publication, mutant enzyme F125T/Y133F
0.15
rac-2-nitro-1-phenylethanol
pH 5.0, temperature not specified in the publication, wild-type enzyme
0.2
rac-2-nitro-1-phenylethanol
pH 5.0, temperature not specified in the publication, mutant enzyme V106F/F125T
0.3
rac-2-nitro-1-phenylethanol
pH 5.0, temperature not specified in the publication, mutant enzyme Y133F
0.6
rac-2-nitro-1-phenylethanol
pH 5.0, temperature not specified in the publication, mutant enzyme F125T
3
rac-mandelonitrile

pH 5.0, temperature not specified in the publication, mutant enzyme I209G
3
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121T
5
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121H
6
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121Q
7
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L152F
7
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme V106F
9
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121S
15
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121V
15
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121W
17
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L148F
20
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121C
20
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L146M
21
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme F210I
22
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme Y133F
23
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme I209A
23
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121A
25
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, wild-type enzyme
32
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme F125T/L146M
32
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme F125T/Y133F
33
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme C81L
33
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121I
43
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121M
43
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121Y/F125T
45
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121Y/F125T/L146M
55
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme V106F/L121Y
66
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme F125T
77
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121F
82
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme V106F/L121Y/F125T
106
rac-mandelonitrile
pH 5.0, temperature not specified in the publication, mutant enzyme L121Y
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0.1
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121P
0.15
substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, mutant enzyme C81L
0.17
substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, mutant enzyme V106F
0.27
substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, mutant enzyme F125T
0.32
substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, mutant enzyme L146M
0.39
substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, mutant enzyme V106F/F125T
0.56
substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, mutant enzyme L121Y/F125T/Y133F
0.62
substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, mutant enzyme L121Y
0.71
substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, mutant enzyme L121Y/F125T/L146M
0.9
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme I12A
1.02
-
C-terminal His-tagged recombinant mutant enzyme H103L expressed in a RTS 100 wheat germ cell-free translation system, using benzaldehyde as substrate, pH and temperature not specified in the publication
1.1
-
recombinant mutant enzyme H103L expressed in Pichia pastoris, using benzaldehyde as substrate, pH and temperature not specified in the publication
1.4
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121G
1.55
-
C-terminal His-tagged recombinant wild type enzyme expressed in a RTS 100 wheat germ cell-free translation system, using benzaldehyde as substrate, pH and temperature not specified in the publication
1.73
-
recombinant wild type enzyme expressed in Escherichia coli JM109 cells, using benzaldehyde as substrate, pH and temperature not specified in the publication
1.97
-
untagged recombinant wild type enzyme expressed in a RTS 100 wheat germ cell-free translation system, using benzaldehyde as substrate, pH and temperature not specified in the publication
1.98
-
untagged recombinant mutant enzyme H103L expressed in a RTS 100 wheat germ cell-free translation system, using benzaldehyde as substrate, pH and temperature not specified in the publication
115
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121Y/L146M
119
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121F
12
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L152F
140
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme V106F/L121Y/F125T
149
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121Y
2
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121T
2.03
-
recombinant wild type enzyme expressed in Leishmania tarentolae, using benzaldehyde as substrate, pH and temperature not specified in the publication
2.1
-
recombinant wild type enzyme expressed in Pichia pastoris, using benzaldehyde as substrate, pH and temperature not specified in the publication
2.18
-
recombinant mutant enzyme H103L expressed in Leishmania tarentolae, using benzaldehyde as substrate, pH and temperature not specified in the publication
22
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme C81L
24
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L146M
28
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme Y133F
29.2
-
recombinant mutant enzyme H103L expressed in Escherichia coli JM109 cells, using benzaldehyde as substrate, pH and temperature not specified in the publication
3.8
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121S
30
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121A
33
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, wild-type enzyme
35
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121I
4
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121H
42
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme I209A
5.1
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme I209G
5.9
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121Q
53
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme F125T/L146M
55
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121Y/F125T
57.2
-
mutant enzyme G113S
6.7
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme V106F
64
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121Y/F125T/L146M
7
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L148F
88
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme V106F/L121Y
0.13

substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, mutant enzyme L121Y/L146M
0.13
substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, wild-type enzyme
0.2

substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, mutant enzyme F125T/L146M
0.2
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121E
0.21

substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, mutant enzyme F125T/Y133F
0.21
substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, mutant enzyme V106F/L146M
0.29

substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, mutant enzyme V106F/L121Y/F125T
0.29
substrate: rac-2-nitro-1-phenylethanol, pH 5.0, temperature not specified in the publication, mutant enzyme Y133F
0.7

substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121N
0.7
-
recombinant mutant enzyme H103L expressed in an Escherichia coli lysate (WakoPURE system), using benzaldehyde as substrate, pH and temperature not specified in the publication
14

substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme F210I
14
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121W
16

substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121C
16
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121V
52

substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme F125T/Y133F
52
substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme L121M
86

-
-
92

substrate: rac-mandelonitrile, pH 5.0, temperature not specified in the publication, mutant enzyme F125T
92
wild-type enzyme from leaves
additional information

-
expressed in Saccharomyces cerevisiae or Pichia pastoris
additional information
screening assay for hydroxynitrile lyases and its application in high-throughput screening of Escherichia coli mutant libraries, semi-quantitative test where the rate of colour formation corresponds to the particular enzyme activity of the sample
additional information
cyanide-based high-throughput screening assay is developed. The assay is useful to detect activity and enantioselectivity of hydroxynitrile lyases theoretically towards any cyanohydrin substrate
additional information
-
no specific activity is detected with recombinant wild type and mutant enzyme H103L when expressed in an Escherichia coli lysate (WakoPURE system) or as N-terminal His6-tagged enzyme in a RTS 100 wheat germ cell-free translation system
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