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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
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?
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
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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
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?
cyanide + thiophene-2-carbaldehyde
(2S)-hydroxy(thiophen-2-yl)ethanenitrile
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-
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?
cyclohexanone cyanohydrin
?
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-
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?
DL-mandelonitrile
benzaldehyde + HCN
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-
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?
ferrocenyl aldehyde + HCN
ferrocenyl-cyanohydrin
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?
furan-3-carbaldehyde + HCN
(2S)-hydroxy(furan-3-yl)ethanenitrile
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92% enantiomeric excess
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?
HCN + (2E)-oct-2-enal
(2S,3E)-2-hydroxynon-3-enenitrile
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-
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?
HCN + (benzyloxy)acetaldehyde
3-(benzyloxy)-(2S)-2-hydroxy-propanenitrile + 3-(benzyloxy)-(2R)-2-hydroxy-propanenitrile
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50% 3-(benzyloxy)-(2S)-2-hydroxy-propanenitrile and 50% 3-(benzyloxy)-(2R)-2-hydroxy-propanenitrile
?
HCN + (E)-2-butenal
(3E)-2-hydroxypent-3-enenitrile
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-
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?
HCN + 1,1'-diformylferrocene
(R,R)-1,1-bis(cyanohydroxymethyl)ferrocene
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-
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?
HCN + 2,2-dimethylpropanal
2-hydroxy-3,3-dimethylbutyronitrile
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-
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?
HCN + 2-allyloxybutanal
3-allyloxy-2-hydroxypentanenitrile
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-
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?
HCN + 2-allyloxyheptanal
(2R,3RS)-3-allyloxy-2-hydroxyoctanenitrile
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-
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?
HCN + 2-allyloxyhexanal
(2R,3RS)-3-allyloxy-2-hydroxyheptanenitrile
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-
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?
HCN + 2-allyloxypentanal
(2R,3RS)-3-allyloxy-2-hydroxyhexanenitrile
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-
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?
HCN + 2-allyloxypropanal
3-allyloxy-2-hydroxybutanenitrile
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-
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?
HCN + 2-benzyloxypropanal
3-benzyloxy-2-hydroxybutanenitrile
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-
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?
HCN + 2-chlorobenzaldehyde
(2-chlorophenyl)(hydroxy)acetonitrile
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-
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?
HCN + 2-hexenal
2-hydroxyhept-3-enenitrile
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-
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?
HCN + 2-methoxymethoxypropanal
3-methoxymethoxy-2-hydroxybutanenitrile
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-
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?
HCN + 2-methylallyloxyacetaldehyde
3-(2-methylallyloxy)-2-hydroxypropionitrile
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-
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?
HCN + 2-methyldihydrofuran
3-hydroxy-2-methyltetrahydrofuran-3-carbonitrile
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analysis of diastereomeric distribution of the products, depending on different reaction conditions such as pH, reaction time, and solvent properties
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?
HCN + 2-methyldihydrothiophen-3(2H)-one
3-hydroxy-2-methyltetrahydrothiophen-3-carbonitrile
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analysis of diastereomeric distribution of the products, depending on different reaction conditions such as pH, reaction time, and solvent properties
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?
HCN + 2-naphthaldehyde
(2S)-2-hydroxynaphthalen-2-yl-acetonitrile + (2R)-2-hydroxynaphthalen-2-yl-acetonitrile
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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
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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
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?
HCN + 3-furaldehyde
(2R)-3-furyl(hydroxy)acetonitrile
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-
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?
HCN + 3-furylcarbaldehyde
hydroxy(fur-3yl)acetonitrile
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-
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?
HCN + 3-phenoxybenzaldehyde
(2S)-hydroxy(3-phenoxyphenyl)acetonitrile
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?
HCN + 3-phenoxypropanal
(2S)-2-hydroxy-4-phenoxybutanenitrile + (2S)-2-hydroxy-4-phenoxybutanenitrile
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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
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?
HCN + acrolein
(2S)-2-hydroxybut-3-enenitrile
HCN + allyloxy-2-hydroxypropionitrile
3-allyloxy-2-hydroxypropionitrile
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?
HCN + benzaldehyde
(R)-mandelonitrile
HCN + benzaldehyde
(S)-mandelonitrile
HCN + benzene-1,2,4-tricarbaldehyde
?
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-
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?
HCN + benzyloxyacetaldehyde
3-benzyloxy-2-hydroxypropionitrile
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-
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?
HCN + cyclohexanecarbaldehyde
(2R)-cyclohexyl(hydroxy)acetonitrile
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?
HCN + decanal
(S)-2-hydroxyundecanenitrile
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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
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?
HCN + dodecanal
(S)-2-hydroxytridecanenitrile
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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
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?
HCN + ferrocene aldehyde
?
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?
HCN + formylferrocene
(R)-(cyanohydroxymethyl)ferrocene
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?
HCN + furaldehyde
(2R)-furan-2-yl(hydroxy)ethanenitrile
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enzyme encapsulated in sol-gel matrix
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?