Information on EC 4.1.2.10 - (R)-mandelonitrile lyase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
4.1.2.10
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RECOMMENDED NAME
GeneOntology No.
(R)-mandelonitrile lyase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(R)-mandelonitrile = cyanide + benzaldehyde
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
carboligation
Prunus pseudoarmeniaca
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cyanohydrin formation
Henry reaction
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transcyanation
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
amygdalin and prunasin degradation
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Biosynthesis of secondary metabolites
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Cyanoamino acid metabolism
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vicianin bioactivation
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SYSTEMATIC NAME
IUBMB Comments
(R)-mandelonitrile benzaldehyde-lyase (cyanide-forming)
A variety of enzymes from different sources and with different properties. Some are flavoproteins, others are not. Active towards a number of aromatic and aliphatic hydroxynitriles (cyanohydrins).
CAS REGISTRY NUMBER
COMMENTARY hide
9024-43-5
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Prunus amygdalus turcomanica
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Prunus pseudoarmeniaca
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Ehrh.
UniProt
Manually annotated by BRENDA team
Prunus sp.
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Manually annotated by BRENDA team
endophytic bacterium Psm-BT4509
UniProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-4-hydroxymandelonitrile
cyanide + 4-hydroxybenzaldehyde
show the reaction diagram
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r
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
2-chlorobenzaldehyde + HCN
(R)-2-chloromandelonitrile
show the reaction diagram
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after 96 h, 100% yield, 21% enantiomeric excess
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?
2-chlorobenzaldehyde + nitromethane
1-(2-chlorophenyl)-2-nitroethanol
show the reaction diagram
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34% yield after 2 h
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?
2-heptanone + HCN
(R)-2-heptanone cyanohydrin
show the reaction diagram
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needs long reaction time (26 h), providing low enantiomeric exess (14%), which supports the fact that methyl ketones of long aliphatic chain are poor substrates
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-
?
2-methoxybenzaldehyde + nitromethane
1-(2-methoxyphenyl)-2-nitroethanol
show the reaction diagram
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13% yield after 2 h
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?
2-methylbenzaldehyde + nitromethane
1-(2-methylphenyl)-2-nitroethanol
show the reaction diagram
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12% yield after 2 h
-
?
3,4-dihydroxybenzaldehyde + HCN
(R)-3,4-dihydroxymandelonitrile
show the reaction diagram
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after 96 h, 100% yield, 99% enantiomeric excess
-
?
3-(2-naphthyl)benzaldehyde + nitromethane
(1R)-1-[3-(naphthalen-2-yl)phenyl]-2-nitroethanol
show the reaction diagram
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7% yield after 2 h
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?
3-chlorobenzaldehyde + nitromethane
1-(3-chlorophenyl)-2-nitroethanol
show the reaction diagram
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17% yield after 2 h
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?
3-methoxybenzaldehyde + nitromethane
1-(3-methoxyphenyl)-2-nitroethanol
show the reaction diagram
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17% yield after 2 h
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?
3-methylbenzaldehyde + nitromethane
1-(3-methylphenyl)-2-nitroethanol
show the reaction diagram
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12% yield after 2 h
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?
3-phenylpropionaldehyde + HCN
(R)-2-hydroxy-4-phenylbutyronitrile
show the reaction diagram
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after 96 h, 83% yield, 91% enantiomeric excess
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?
4-bromobenzaldehyde + HCN
(R)-4-bromomandelonitrile
show the reaction diagram
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after 96 h, 100% yield, 99% enantiomeric excess
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?
4-bromobenzaldehyde + nitromethane
1-(4-bromophenyl)-2-nitroethanol
show the reaction diagram
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20% yield after 2 h
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?
4-chlorobenzaldehyde + nitromethane
1-(4-chlorophenyl)-2-nitroethanol
show the reaction diagram
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9% yield after 2 h
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?
4-fluorobenzaldehyde + HCN
(R)-4-fluoroonitrile
show the reaction diagram
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after 96 h, 100% yield, 72% enantiomeric excess
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?
4-fluorobenzaldehyde + nitromethane
1-(4-fluorophenyl)-2-nitroethanol
show the reaction diagram
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9% yield after 2 h
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?
4-methoxybenzaldehyde + nitromethane
1-(4-methoxyphenyl)-2-nitroethanol
show the reaction diagram
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2% yield after 2 h
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?
4-methylbenzaldehyde + nitromethane
1-(4-methylphenyl)-2-nitroethanol
show the reaction diagram
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11% yield after 2 h
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?
4-nitrobenzaldehyde + HCN
(R)-4-nitromandelonitrile
show the reaction diagram
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after 96 h, 100% yield, 14% enantiomeric excess
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?
acetyltrimethylsilane + acetone cyanohydrin
?
show the reaction diagram
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both acetyltrimethylsilane conversion and enantiomeric excess of the product are above 99%
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?
benzaldehyde + HCN
(R)-mandelonitrile
show the reaction diagram
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after 96 h, 100% yield, 99% enantiomeric excess
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?
benzaldehyde + nitromethane
(R)-2-nitro-1-phenylethanol
show the reaction diagram
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30% yield after 2 h
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?
cyanide + (2E)-3-methylpent-2-enal
(2R,3E)-2-hydroxy-4-methylhex-3-enenitrile
show the reaction diagram
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?
cyanide + (2E)-hex-2-enal
(2R,3E)-2-hydroxyhept-3-enenitrile
show the reaction diagram
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?
cyanide + (2E)-hex-2-enal
(3E)-2-hydroxyhept-3-enenitrile
show the reaction diagram
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53% enantiomeric excess
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?
cyanide + (2E,4E)-hexa-2,4-dienal
(2R,3E,5E)-2-hydroxyhepta-3,5-dienenitrile
show the reaction diagram
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?
cyanide + (4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
(2S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
show the reaction diagram
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the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde is converted to 47.1% (2S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 52.9% (2R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
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?
cyanide + (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde
(2S)-hydroxy-[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile + (2R)-hydroxy-[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
show the reaction diagram
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the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde is converted to 34.2% (2S)-hydroxy[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile and 65.8% (2R)-hydroxy[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
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?
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
show the reaction diagram
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the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde is converted to 48.2% (2S)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 51.8% (2R)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
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?
cyanide + (4S)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
(2S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
show the reaction diagram
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the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4S)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde is converted to 66.4% (2S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 33.6% (2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
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?
cyanide + (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde
(2S)-hydroxy-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile + (2R)-hydroxy-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
show the reaction diagram
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the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde is converted to 52.6% (2S)-hydroxy[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile and 47.4% (2R)-hydroxy[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
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?
cyanide + (4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde
(2S)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
show the reaction diagram
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the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde is converted to 49.3% (2S)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 50.7% (2R)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
?
cyanide + (benzyloxy)acetaldehyde
(2R)-3-(benzyloxy)-2-hydroxypropanenitrile + (2S)-3-(benzyloxy)-2-hydroxypropanenitrile
show the reaction diagram
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43.9% (2S)-3-(benzyloxy)-2-hydroxypropanenitrile and 53.1% (2S)-3-(benzyloxy)-2-hydroxypropanenitrile
-
?
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
show the reaction diagram
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the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate 1,4-dioxaspiro[4.5]decane-2-carbaldehyde is converted to 21.8% (2S)-(2R)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile, 28.3% (2R)-(2R)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile, 30.3% (2S)-(2S)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile and 19.6% (2R)-(2S)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile
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?
cyanide + 1-phenylethanone
(2R)-2-hydroxy-2-phenylpropanenitrile
show the reaction diagram
cyanide + 2,2-dimethylpropanal
(2R)-2-hydroxy-3,3-dimethylbutanenitrile
show the reaction diagram
-
activity is 33% of the activity with benzaldehyde
9% enentiomeric excess
-
?
cyanide + 2-(benzyloxy)-3-phenylpropanal
(2S,3S)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile + (2R,3S)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile + (2S,3R)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile + (2R,3R)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile
show the reaction diagram
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26.9% (2S,3S)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile, 23.4% (2R,3S)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile, 29.2% (2S,3R)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile and 20.6% (2R,3R)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile
-
?
cyanide + 2-(benzyloxy)propanal
(2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile + (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile + (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile + (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile
show the reaction diagram
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45.4% (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile, 8.1% (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile, 33.3% (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile and 13.3% (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile
-
?
cyanide + 2-(naphthalen-2-yl)propanal
(2S,3S)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile + (2S,3R)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile + (2R,3S)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile + (2R,3R)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile
show the reaction diagram
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30.4% (2S,3S)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile, 24.0% (2S,3R)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile, 20.0% (2R,3S)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile and 25.6% (2R,3R)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile
-
?
cyanide + 2-bromobenzaldehyde
(2R)-(2-bromophenyl)(hydroxy)ethanenitrile
show the reaction diagram
-
98% enantiomeric excess
-
?
cyanide + 2-chlorobenzaldehyde
(2R)-(2-chlorophenyl)(hydroxy)ethanenitrile
show the reaction diagram
cyanide + 2-chlorobenzaldehyde
(R)-2-chloromandelonitrile
show the reaction diagram
cyanide + 2-fluorobenzaldehyde
(2R)-(2-fluorophenyl)(hydroxy)ethanenitrile
show the reaction diagram
-
99% enantiomeric excess
-
?
cyanide + 2-iodobenzaldehyde
(2R)-(2-iodophenyl)(hydroxy)ethanenitrile
show the reaction diagram
-
more than 95% enantiomeric excess
-
?
cyanide + 2-methoxy-3-phenylpropanal
(2S,3S)-2-hydroxy-3-methoxy-4-phenylbutanenitrile + (2R,3S)-2-hydroxy-3-methoxy-4-phenylbutanenitrile + (2S,3R)-2-hydroxy-3-methoxy-4-phenylbutanenitrile + (2R,3R)-2-hydroxy-3-methoxy-4-phenylbutanenitrile
show the reaction diagram
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43.1% (2S,3S)-2-hydroxy-3-methoxy-4-phenylbutanenitrile, 8.4 (2R,3S)-2-hydroxy-3-methoxy-4-phenylbutanenitrile, 40.1% (2S,3R)-2-hydroxy-3-methoxy-4-phenylbutanenitrile and 8.4% (2R,3R)-2-hydroxy-3-methoxy-4-phenylbutanenitrile
-
?
cyanide + 2-methylpropanal
(2R)-2-hydroxy-3-methylbutanenitrile
show the reaction diagram
-
activity is 67% of the activity with benzaldehyde
13% enentiomeric excess
-
?
cyanide + 2-naphthaldehyde
(R)-2-hydroxy-2-(naphthalen-2-yl)acetonitrile
show the reaction diagram
-
-
-
?
cyanide + 2-phenylpropanal
(2R,3S)-2-hydroxy-3-phenylbutanenitrile + (2S,3R)-2-hydroxy-3-phenylbutanenitrile + (2R,3R)-2-hydroxy-3-phenylbutanenitrile
show the reaction diagram
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3.0% (2S,3S)-2-hydroxy-3-phenylbutanenitrile, 51.8% (2R,3S)-2-hydroxy-3-phenylbutanenitrile, 27.6% (2S,3R)-2-hydroxy-3-phenylbutanenitrile and + 17.6% (2R,3R)-2-hydroxy-3-phenylbutanenitrile
-
?
cyanide + 3,4-dihydro-1H-isochromene-3-carbaldehyde
(S)-2-hydroxy-2-((S)-isochroman-3-yl)acetonitrile + (S)-2-hydroxy-2-((R)-isochroman-3-yl)acetonitrile + (R)-2-hydroxy-2-((S)-isochroman-3-yl)acetonitrile + (R)-2-hydroxy-2-((R)-isochroman-3-yl)acetonitrile
show the reaction diagram
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-
28.6% (2S)-(3S)-3,4-dihydro-1H-isochromen-3-yl(hydroxy)ethanenitrile, 21.5% (2R)-(3S)-3,4-dihydro-1H-isochromen-3-yl(hydroxy)ethanenitrile, 28.7% (2S)-(3R)-3,4-dihydro-1H-isochromen-3-yl(hydroxy)ethanenitrile and 21.1% (2R)-(3R)-3,4-dihydro-1H-isochromen-3-yl(hydroxy)ethanenitrile
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?
cyanide + 3,4-dihydroxybenzaldehyde
(R)-3,4-dihydroxymandelonitrile
show the reaction diagram
Prunus amygdalus turcomanica
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-
-
?
cyanide + 3-bromobenzaldehyde
(2R)-(3-bromophenyl)(hydroxy)ethanenitrile
show the reaction diagram
-
95% enantiomeric excess
-
?
cyanide + 3-chlorobenzaldehyde
(2R)-(3-chlorophenyl)(hydroxy)ethanenitrile
show the reaction diagram
-
more than 99% enantiomeric excess
-
?
cyanide + 3-fluorobenzaldehyde
(2R)-(3-fluorophenyl)(hydroxy)ethanenitrile
show the reaction diagram
-
more than 99% enantiomeric excess
-
?
cyanide + 3-hydroxy-2,2-dimethylpropanal
(2R)-2,5-dihydroxy-3,3-dimethylpentanenitrile
show the reaction diagram
-
i.e. hydroxypivaldehyde
best enantiomeric excess is obtained at pH 2.5
-
?
cyanide + 3-iodobenzaldehyde
(2R)-(3-iodophenyl)(hydroxy)ethanenitrile
show the reaction diagram
-
93% enantiomeric excess
-
?
cyanide + 3-methoxy-3-phenylpropanal
(2S,4S)-2-hydroxy-4-methoxy-4-phenylbutanenitrile + (2R,4S)-2-hydroxy-4-methoxy-4-phenylbutanenitrile + (2S,4R)-2-hydroxy-4-methoxy-4-phenylbutanenitrile + (2R,4R)-2-hydroxy-4-methoxy-4-phenylbutanenitrile
show the reaction diagram
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6.5% (2S,4S)-2-hydroxy-4-methoxy-4-phenylbutanenitrile, 45.2% (2R,4S)-2-hydroxy-4-methoxy-4-phenylbutanenitrile, 14.0% (2S,4R)-2-hydroxy-4-methoxy-4-phenylbutanenitrile, 34.3% (2R,4R)-2-hydroxy-4-methoxy-4-phenylbutanenitrile
-
?
cyanide + 3-phenoxybenzaldehyde
(2R)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
show the reaction diagram
-
more than 95% enantiomeric excess
-
?
cyanide + 3-phenoxypropanal
(2R)-2-hydroxy-5-phenylpentanenitrile
show the reaction diagram
-
-
74.3% (2R)-2-hydroxy-5-phenylpentanenitrile and 25.7% (2S)-2-hydroxy-5-phenylpentanenitrile
-
?
cyanide + 3-phenylpropanal
(2R)-2-hydroxy-4-phenylbutanenitrile
show the reaction diagram
-
68% enantiomeric excess
-
?
cyanide + 3-tetrahydrothiophenone
(S)-3-hydroxytetrahydrothiophene-3-carbonitrile
show the reaction diagram
-
the enzyme, that shows (R)-stereospecificity for its natural substrate shows S-stereselectivity with the heterocyclic ketone as substrate
-
-
?
cyanide + 4-bromobenzaldehyde
(2R)-(4-bromophenyl)(hydroxy)ethanenitrile
show the reaction diagram
-
more than 99% enantiomeric excess
-
?
cyanide + 4-chlorobenzaldehyde
(2R)-(4-chlorophenyl)(hydroxy)ethanenitrile
show the reaction diagram
-
more than 99% enantiomeric excess
-
?
cyanide + 4-fluorobenzaldehyde
(2R)-(4-fluorophenyl)(hydroxy)ethanenitrile
show the reaction diagram
-
more than 99% enantiomeric excess
-
?
cyanide + 4-hydroxybenzaldehyde
(2R)-(4-hydroxyphenyl)(hydroxy)ethanenitrile
show the reaction diagram
-
97% enantiomeric excess
-
?
cyanide + 4-hydroxybenzaldehyde
(R)-4-hydroxymandelonitrile
show the reaction diagram
-
-
-
-
r
cyanide + 4-hydroxybutanal
(R)-2,5-dihydroxypentanenitrile
show the reaction diagram
-
by varying the different reaction parameters it is possible to reduce the extension of the undesirable non-enzymatic competing reactions and optimize the optical purity of the cyanohydrin product. Best results are obtained at 15C
-
-
?
cyanide + 4-iodobenzaldehyde
(2R)-(4-iodophenyl)(hydroxy)ethanenitrile
show the reaction diagram
-
92% enantiomeric excess
-
?
cyanide + 4-methoxybenzaldehyde
(2R)-(4-methoxyphenyl)(hydroxy)ethanenitrile
show the reaction diagram
-
68% enantiomeric excess
-
?
cyanide + 4-methoxybenzaldehyde
(2R)-hydroxy(4-methoxyphenyl)ethanenitrile
show the reaction diagram
cyanide + 4-phenylbutan-2-one
2-hydroxy-4-phenylbutyronitrile
show the reaction diagram
Prunus amygdalus turcomanica
-
-
-
-
?
cyanide + 4-phenylbutanal
(2R)-2-hydroxy-5-phenylpentanenitrile
show the reaction diagram
-
-
88.9% (2R)-2-hydroxy-5-phenylpentanenitrile and 11.1% (2S)-2-hydroxy-5-phenylpentanenitrile
-
?
cyanide + 5-hydroxypentanal
(R)-2,6-dihydroxyhexanenitrile
show the reaction diagram
-
by varying the different reaction parameters it is possible to reduce the extension of the undesirable non-enzymatic competing reaction and optimize the optical purity of the cyanohydrin product. Best results are obtained at 15C
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-
?
cyanide + 6-methylhept-5-en-2-one
(2R)-2-hydroxy-2,6-dimethylhept-5-enenitrile
show the reaction diagram
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
cyanide + butanal
(2R)-2-hydroxypentanenitrile
show the reaction diagram
cyanide + cinnamaldehyde
(2R,3E)-2-hydroxy-4-phenylbut-3-enenitrile
show the reaction diagram
-
i.e. (2E)-3-phenylprop-2-enal
-
-
?
cyanide + cyclohexanecarbaldehyde
(2R)-cyclohexyl(hydroxy)acetonitrile
show the reaction diagram
-
activity is 41% of the activity with benzaldehyde
10% enentiomeric excess
-
?
cyanide + cyclohexanone
1-hydroxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
?
cyanide + decanal
(2R)-2-hydroxyundecanal
show the reaction diagram
-
56% enantiomeric excess
-
?
cyanide + furan-2-carbaldehyde
(2R)-furan-2-yl(hydroxy)ethanenitrile
show the reaction diagram
cyanide + hexan-2-one
(2R)-2-hydroxy-2-methylhexanenitrile
show the reaction diagram
cyanide + hexanal
(2R)-2-hydroxyheptanenitrile
show the reaction diagram
-
98% enantiomeric excess
-
?
cyanide + isobutyraldehyde
2-hydroxy-3-methylbutyronitrile
show the reaction diagram
-
-
-
?
cyanide + naphthalen-2-ylacetaldehyde
(2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
show the reaction diagram
-
-
3.5% (2S)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile and 96.5% (2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
-
?
cyanide + naphthalen-2-ylacetaldehyde
(2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile + (2S)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
show the reaction diagram
-
-
33.2% (2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile and 66.8% (2S)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
-
?
cyanide + naphthalene-2-carbaldehyde
(2R)-hydroxy(naphthalen-2-yl)ethanenitrile
show the reaction diagram
-
-
97.6% (2R)-hydroxy(naphthalen-2-yl)ethanenitrile and 2.4% (2S)-hydroxy(naphthalen-2-yl)ethanenitrile
-
?
cyanide + p-anisaldehyde
(R)-2-hydroxy-2-(4-methoxyphenyl)acetonitrile
show the reaction diagram
-
-
-
?
cyanide + pentan-2-one
(2R)-2-hydroxy-2-methylpentanenitrile
show the reaction diagram
cyanide + phenylacetaldehyde
(2R)-2-hydroxy-3-phenylpropanenitrile
show the reaction diagram
cyanide + piperonal
(R)-2-hydroxy-2-(3,4-methylenedioxyphenyl)acetonitrile
show the reaction diagram
-
-
-
?
cyanide + pivaldehyde
pivaloyl cyanide
show the reaction diagram
-
-
-
?
cyanide + propanal
(2R)-2-hydroxybutanenitrile
show the reaction diagram
-
activity is 20% of the activity with benzaldehyde
7% enentiomeric excess
-
?
cyanide + propionaldehyde
2-hydroxybutyronitrile
show the reaction diagram
-
-
-
?
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
show the reaction diagram
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate tetrahydro-2H-pyran-2-carbaldehyde is converted to 47.6% (2S)-hydroxy[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile, 4.6% (2R)-hydroxy[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile, 42.6% (2S)-hydroxy[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile and 5.2% (2R)-hydroxy[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile
-
?
cyanide + tetrahydrofuran-2-carbaldehyde
(2S)-hydroxy-[(2R)-tetrahydrofuran-2-yl]ethanenitrile + (2R)-hydroxy-[(2R)-tetrahydrofuran-2-yl]ethanenitrile + (2S)-hydroxy-[(2S)-tetrahydrofuran-2-yl]ethanenitrile + (2R)-hydroxy-[(2S)-tetrahydrofuran-2-yl]ethanenitrile
show the reaction diagram
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate tetrahydrofuran-2-carbaldehyde is converted to 33.7% (2S)-hydroxy[(2R)-tetrahydrofuran-2-yl]ethanenitrile, 16.2% (2R)-hydroxy[(2R)-tetrahydrofuran-2-yl]ethanenitrile, 35.6% (2S)-hydroxy[(2S)-tetrahydrofuran-2-yl]ethanenitrile and 14.5% (2R)-hydroxy[(2S)-tetrahydrofuran-2-yl]ethanenitrile
-
?
cyanide + thiophene-2-carbaldehyde
(2R)-hydroxy(thiophen-2-yl)ethanenitrile
show the reaction diagram
cyanide + thiophene-2-carbaldehyde
(2S)-hydroxy(thiophen-2-yl)ethanenitrile
show the reaction diagram
-
activity is 2fold higher than with benzaldehyde
75% enentiomeric excess, The (S)-configuration is due to the Cahn-Ingold-Prelog rules
-
?
cyanide + thiophene-2-carbaldehyde
hydroxy(thiophen-2-yl)ethanenitrile
show the reaction diagram
-
separation of enantiomers not posible
-
?
HCN + 1-naphthalenecarboxaldehyde
(R)-2-hydroxy-2-(1-naphthyl)acetonitrile
show the reaction diagram
-
60% conversion
93% enantiomeric excess
-
?
HCN + 2,3,4,5-tetrafluorobenzaldehyde
(R)-2-hydroxy-2-(2,3,4,5-tetrafluorophenyl)acetonitrile
show the reaction diagram
-
26% conversion
23% enantiomeric excess
-
?
HCN + 2,3,4-trimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3,4-trimethoxyphenyl)acetonitrile
show the reaction diagram
-
14% conversion
% enantiomeric excess
-
?
HCN + 2,3,5,6-tetrafluorobenzaldehyde
(R)-2-hydroxy-2-(2,3,5,6-tetrafluorophenyl)acetonitrile
show the reaction diagram
-
21% conversion
12% enantiomeric excess
-
?
HCN + 2,3,5-trimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3,5-trimethoxyphenyl)acetonitrile
show the reaction diagram
-
16% conversion
28% enantiomeric excess
-
?
HCN + 2,3-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,3-dichlorophenyl)acetonitrile
show the reaction diagram
-
11% conversion
22% enantiomeric excess
-
?
HCN + 2,3-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3-dimethoxyphenyl)acetonitrile
show the reaction diagram
-
7% conversion
37% enantiomeric excess
-
?
HCN + 2,4-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,4-dichlorophenyl)acetonitrile
show the reaction diagram
-
13% conversion
78% enantiomeric excess
-
?
HCN + 2,4-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,4-dimethoxyphenyl)acetonitrile
show the reaction diagram
-
11% conversion
48% enantiomeric excess
-
?
HCN + 2,4-dimethylbenzaldehyde
(R)-2-hydroxy-2-(2,4-dimethylphenyl)acetonitrile
show the reaction diagram
-
5.8% conversion
86% enantiomeric excess
-
?
HCN + 2,5-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,5-dichlorophenyl)acetonitrile
show the reaction diagram
-
8.8% conversion
57% enantiomeric excess
-
?
HCN + 2,5-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,5-dimethoxyphenyl)acetonitrile
show the reaction diagram
-
9% conversion
63% enantiomeric excess
-
?
HCN + 2,6-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,6-dichlorophenyl)acetonitrile
show the reaction diagram
-
10% conversion
12% enantiomeric excess
-
?
HCN + 2,6-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,6-dimethoxyphenyl)acetonitrile
show the reaction diagram
-
6.5% conversion
32% enantiomeric excess
-
?
HCN + 2-allylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-allylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-allylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-allylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-allyloxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-allyloxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-allyloxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-allyloxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-butanone
(R)-2-hydroxy-2-methylbutyronitrile
show the reaction diagram
-
48% conversion
72% enantiomeric excess
-
?
HCN + 2-chlorobenzaldehyde
(R)-2-hydroxy-2-(2-chlorophenyl)acetonitrile
show the reaction diagram
HCN + 2-decanone
(R)-2-hydroxy-2-methyl-decanenitrile
show the reaction diagram
-
18% conversion
52% enantiomeric excess
-
?
HCN + 2-ethoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-ethoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-ethoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-ethoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-ethylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-ethylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-ethylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-methylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-furancarboxaldehyde
(S)-2-hydroxy-2-(2-furyl)acetonitrile
show the reaction diagram
-
1.2% conversion
98% enantiomeric excess
-
?
HCN + 2-heptanone
(R)-2-hydroxy-2-methyl-heptanenitrile
show the reaction diagram
-
39% conversion
74% enantiomeric excess
-
?
HCN + 2-hexanone
(R)-2-hydroxy-2-methyl-hexanenitrile
show the reaction diagram
-
48% conversion
80% enantiomeric excess
-
?
HCN + 2-methoxybenzaldehyde
(R)-2-hydroxy-2-(2-methoxyphenyl)acetonitrile
show the reaction diagram
-
6.0% conversion
41% enantiomeric excess
-
?
HCN + 2-methoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-methoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-methoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-methoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-methylbenzaldehyde
(R)-2-hydroxy-2-(2-methylphenyl)acetonitrile
show the reaction diagram
-
6% conversion
61% enantiomeric excess
-
?
HCN + 2-methylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-methylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-methylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-methylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-n-propoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-n-propoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-n-propoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-n-propoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-n-propylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-n-propylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-n-propylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-n-propylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 2-naphthalenecarboxaldehyde
(R)-2-hydroxy-2-(2-naphthyl)acetonitrile
show the reaction diagram
-
58% conversion
98% enantiomeric excess
-
?
HCN + 2-nonanone
(R)-2-hydroxy-2-methyl-nonanenitrile
show the reaction diagram
-
20% conversion
65% enantiomeric excess
-
?
HCN + 2-octanone
(R)-2-hydroxy-2-methyl-octanenitrile
show the reaction diagram
-
22% conversion
67% enantiomeric excess
-
?
HCN + 2-pentanone
(R)-2-hydroxy-2-methyl-pentanenitrile
show the reaction diagram
-
46% conversion
81% enantiomeric excess
-
?
HCN + 2-pyridinecarboxyaldehyde
(S)-2-hydroxy-2-(2-pyridyl)acetonitrile
show the reaction diagram
-
89% conversion
22% enantiomeric excess
-
?
HCN + 2-quinolinecarboxaldehyde
(S)-2-hydroxy-2-(2-quinolinyl)acetonitrile
show the reaction diagram
-
38% conversion
21% enantiomeric excess
-
?
HCN + 2-thiophenecarboxaldehyde
(S)-2-hydroxy-2-(2-thiophenyl)acetonitrile
show the reaction diagram
-
31% conversion
88% enantiomeric excess
-
?
HCN + 2-trifluoromethylbenzaldehyde
(R)-2-hydroxy-2-(2-trifluoromethylphenyl)acetonitrile
show the reaction diagram
-
72% conversion
5% enantiomeric excess
-
?
HCN + 2-undecanone
(R)-2-hydroxy-2-methyl-undecanenitrile
show the reaction diagram
-
21% conversion
31% enantiomeric excess
-
?
HCN + 3,3-dimethyl-2-butanone
(R)-2-hydroxy-2,3,3-trimethyl-butyronitrile
show the reaction diagram
-
28% conversion
38% enantiomeric excess
-
?
HCN + 3,4,5-trimethoxybenzaldehyde
(R)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)acetonitrile
show the reaction diagram
-
24% conversion
31% enantiomeric excess
-
?
HCN + 3,4-dichlorobenzaldehyde
(R)-2-hydroxy-2-(3,4-dichlorophenyl)acetonitrile
show the reaction diagram
-
7.9% conversion
94% enantiomeric excess
-
?
HCN + 3,4-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(3,4-dimethoxyphenyl)acetonitrile
show the reaction diagram
-
13% conversion
78% enantiomeric excess
-
?
HCN + 3,5-dichlorobenzaldehyde
(R)-2-hydroxy-2-(3,5-dichlorophenyl)acetonitrile
show the reaction diagram
-
21% conversion
92% enantiomeric excess
-
?
HCN + 3,5-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(3,5-dimethoxyphenyl)acetonitrile
show the reaction diagram
-
17% conversion
97% enantiomeric excess
-
?
HCN + 3-chlorobenzaldehyde
(R)-2-hydroxy-2-(3-chlorophenyl)acetonitrile
show the reaction diagram
-
38% conversion
92% enantiomeric excess
-
?
HCN + 3-methoxybenzaldehyde
(R)-2-hydroxy-2-(3-methoxyphenyl)acetonitrile
show the reaction diagram
-
31% conversion
92% enantiomeric excess
-
?
HCN + 3-methoxycyclohexanone
cis-(1R,3S)-1-hydroxy-3-methoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 3-methoxycyclohexanone
trans-(1R,3R)-1-hydroxy-3-methoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 3-methyl-2-butanone
(R)-2-hydroxy-2,3-dimethyl-butyronitrile
show the reaction diagram
-
39% conversion
42% enantiomeric excess
-
?
HCN + 3-methylbenzaldehyde
(R)-2-hydroxy-2-(3-methylphenyl)acetonitrile
show the reaction diagram
-
7.5% conversion
87% enantiomeric excess
-
?
HCN + 3-methylcyclohexanone
cis-(1R,3S)-1-hydroxy-3-methylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 3-methylcyclohexanone
trans-(1R,3R)-1-hydroxy-3-methylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 3-nitrobenzaldehyde
(R)-2-hydroxy-2-(3-nitrophenyl)acetonitrile
show the reaction diagram
-
87% conversion
65% enantiomeric excess
-
?
HCN + 3-phenoxybenzaldehyde
(R)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
show the reaction diagram
-
42% conversion
more than 99% enantiomeric excess
-
?
HCN + 3-pyridinecarboxyaldehyde
(R)-2-hydroxy-2-(3-pyridyl)acetonitrile
show the reaction diagram
-
90% conversion
75% enantiomeric excess
-
?
HCN + 3-trifluoromethylbenzaldehyde
(R)-2-hydroxy-2-(3-trifluoro-methylphenyl)acetonitrile
show the reaction diagram
-
91% conversion
68% enantiomeric excess
-
?
HCN + 3-trifluoromethylcyclohexanone
cis-(1R,3S)-1-hydroxy-3-trifluoromethylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 3-trifluoromethylcyclohexanone
trans-(1R,3R)-1-hydroxy-3-trifluoromethylcyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + 4-allyloxybenzaldehyde
(R)-2-hydroxy-2-(4-allyloxyphenyl)acetonitrile
show the reaction diagram
-
6.4% conversion
98% enantiomeric excess
-
?
HCN + 4-benzyloxybenzaldehyde
(R)-2-hydroxy-2-(4-benzyloxyphenyl)acetonitrile
show the reaction diagram
-
5.8% conversion
98% enantiomeric excess
-
?
HCN + 4-bromobenzaldehyde
(R)-2-hydroxy-2-(4-bromophenyl)acetonitrile
show the reaction diagram
-
22% conversion
99% enantiomeric excess
-
?
HCN + 4-chlorbenzaldehyde
(R)-2-hydroxy-2-(4-chlorophenyl)acetonitrile
show the reaction diagram
HCN + 4-fluorobenzaldehyde
(R)-2-hydroxy-2-(4-fluorophenyl)acetonitrile
show the reaction diagram
-
28% conversion
% enantiomeric excess
-
?
HCN + 4-methoxybenzaldehyde
(R)-2-hydroxy-2-(4-methoxyphenyl)acetonitrile
show the reaction diagram
-
17% conversion
97% enantiomeric excess
-
?
HCN + 4-methyl-2-pentanone
(R)-2-hydroxy-2,4-dimethyl-pentanenitrile
show the reaction diagram
-
40% conversion
88% enantiomeric excess
-
?
HCN + 4-methylbenzaldehyde
(R)-2-hydroxy-2-(4-methylphenyl)acetonitrile
show the reaction diagram
-
7.0% conversion
95% enantiomeric excess
-
?
HCN + 4-nitrobenzaldehyde
(R)-2-hydroxy-2-(4-nitrophenyl)acetonitrile
show the reaction diagram
-
89% conversion
71% enantiomeric excess
-
?
HCN + 4-phenoxybenzaldehyde
(R)-2-hydroxy-2-(4-phenoxyphenyl)acetonitrile
show the reaction diagram
-
-
-
?
HCN + 4-pyridinecarboxyaldehyde
(R)-2-hydroxy-2-(4-pyridyl)acetonitrile
show the reaction diagram
-
65% conversion
41% enantiomeric excess
-
?
HCN + 4-quinolinecarboxaldehyde
(R)-2-hydroxy-2-(4-quinolinyl)acetonitrile
show the reaction diagram
-
73% conversion
28% enantiomeric excess
-
?
HCN + 4-tert-butyldimethylsilyloxybenzaldehyde
(R)-2-hydroxy-2-(4-tert-butyldimethylsilyloxyphenyl)acetonitrile
show the reaction diagram
-
4.8% conversion
97% enantiomeric excess
-
?
HCN + 4-trifluoromethylbenzaldehyde
(R)-2-hydroxy-2-(4-trifluoromethylphenyl)acetonitrile
show the reaction diagram
-
90% conversion
76% enantiomeric excess
-
?
HCN + 5-methyl-2-hexanone
(R)-2-hydroxy-2,5-dimethyl-hexanenitrile
show the reaction diagram
-
30% conversion
76% enantiomeric excess
-
?
HCN + acetophenone
2-hydroxyphenylpropionitrile
show the reaction diagram
-
-
-
-
?
HCN + benzaldehyde
(R)-2-hydroxy-2-phenylacetonitrile
show the reaction diagram
-
-
-
-
?
HCN + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
HCN + butanal
(R)-2-hydroxy-pentanenitrile
show the reaction diagram
-
51% conversion
84% enantiomeric excess
-
?
HCN + cyclohexanecarboxaldehyde
(R)-2-hydroxy-2-cyclohexyl-acetonitrile
show the reaction diagram
-
54% conversion
94% enantiomeric excess
-
?
HCN + cyclopentanecarboxaldehyde
(R)-2-hydroxy-2-cyclopentyl-acetonitrile
show the reaction diagram
-
51% conversion
91% enantiomeric excess
-
?
HCN + decanal
(R)-2-hydroxyundecanenitrile
show the reaction diagram
-
reaction in a two phase solvent system aqueous buffer and ionic liquid. When compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remains good
-
-
?
HCN + dodecanal
(R)-2-hydroxytridecanenitrile
show the reaction diagram
-
reaction in a two phase solvent system aqueous buffer and ionic liquid. When compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remains good
-
-
?
HCN + hexanal
(R)-2-hydroxy-octanenitrile
show the reaction diagram
-
38% conversion
81% enantiomeric excess
-
?
HCN + iso-propoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-iso-propoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + iso-propoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-iso-propoxycyclohexanecarbonitrile
show the reaction diagram
-
-
-
-
?
HCN + isobutyraldehyde
(R)-2-hydroxy-3-methyl-butyronitrile
show the reaction diagram
-
43% conversion
88% enantiomeric excess
-
?
HCN + pentanal
(R)-2-hydroxy-hexanenitrile
show the reaction diagram
-
36% conversion
85% enantiomeric excess
-
?
HCN + piperonal
(R)-2-hydroxy-2-(3,4-methylenedioxyphenyl)acetonitrile
show the reaction diagram
-
34% conversion
98% enantiomeric excess
-
?
HCN + pivaldehyde
(R)-2-hydroxy-3,3-dimethyl-butyronitrile
show the reaction diagram
-
29% conversion
92% enantiomeric excess
-
?
HCN + propanal
(R)-2-hydroxy-butyronitrile
show the reaction diagram
-
48% conversion
78% enantiomeric excess
-
?
HCN + trimethylsilylmethylketone
(R)-2-hydroxy-2-trimethylsilyl-propanenitrile
show the reaction diagram
-
62% conversion
72% enantiomeric excess
-
?
HCN + undecanal
(R)-2-hydroxydodecanenitrile
show the reaction diagram
-
reaction in a two phase solvent system aqueous buffer and ionic liquid. When compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remains good
-
-
?
nitromethane + 2-chlorobenzaldehyde
(1R)-1-(2-chlorophenyl)-2-nitroethanol
show the reaction diagram
-
-
34% yield, 68% enantiomeric excess
-
?
nitromethane + 3-methoxybenzaldehyde
(1R)-1-(3-methoxyphenyl)-2-nitroethanol
show the reaction diagram
-
-
17% yield, 91% enantiomeric excess
-
?
nitromethane + 4-fluorobenzaldehyde
(1R)-1-(4-fluorophenyl)-2-nitroethanol
show the reaction diagram
-
-
20% yield, 81% enantiomeric excess
-
?
nitromethane + benzaldehyde
(1R)-2-nitro-1-phenylethanol
show the reaction diagram
-
30% yield, 91% enantiomeric excess
-
-
?
propiophenone + HCN
(S)-1-phenylacetone cyanohydrin
show the reaction diagram
-
with 24% conversion and 46% enantiomeric exess
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(R)-mandelonitrile
cyanide + benzaldehyde
show the reaction diagram
cyanide + benzaldehyde
(R)-mandelonitrile
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
not a flavoprotein
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
metal ions are not required for its activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-Iodoacetamide
1 mM, 9% residual activity; 9.0% residual activity at 1 mM
2-mercaptoethanol
Ag+
1 mM, 8% residual activity; 8.2 residual activity at 1 mM
CuSO4
1 mM, 100% inhibition
diethyl dicarbonate
diethyldicarbonate
diisopropyl fluorophosphate
-
2 mM, 80% inhibition
FeCl3
1 mM, 50% inhibition
Hg2+
1 mM, 9% residual activity; 9.0% residual activity at 1 mM
HgCl2
1 mM, 100% inhibition
iodoacetamide
-
2 mM, 70% inhibition
iodoacetic acid
NH2OH
82.7% residual activity at 1 mM
p-chloromercuribenzoic acid
58.6% residual activity at 10 mM
phenylmethylsulfonyl fluoride
Phenylmethylsulfonylfluoride
1 mM, 59% inhibition
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.4
(R)-4-hydroxymandelonitrile
-
pH 5.0, 25C
0.161 - 10.3
(R)-Mandelonitrile
1.1
2-naphthaldehyde
pH 5.5
6
4-hydroxybenzaldehyde
-
pH 5.0, 25C
0.83 - 41
benzaldehyde
41.8
Isobutyraldehyde
pH 5.5
3.5
p-anisaldehyde
pH 5.5
2.6
piperonal
pH 5.5
39.3
pivaldehyde
pH 5.5
99.9
propionaldehyde
pH 5.5
additional information
additional information
-
estimation of kinetic parameters by progress curve analysis
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.03 - 56
(R)-Mandelonitrile
1160
2-naphthaldehyde
Eriobotrya japonica
B7VF77
pH 5.5
1700
benzaldehyde
Eriobotrya japonica
B7VF77
pH 5.5
110
Isobutyraldehyde
Eriobotrya japonica
B7VF77
pH 5.5
582
p-anisaldehyde
Eriobotrya japonica
B7VF77
pH 5.5
334
piperonal
Eriobotrya japonica
B7VF77
pH 5.5
164
pivaldehyde
Eriobotrya japonica
B7VF77
pH 5.5
223
propionaldehyde
Eriobotrya japonica
B7VF77
pH 5.5
additional information
additional information
Prunus dulcis
-
estimation of kinetic parameters by progress curve analysis
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
348
(R)-Mandelonitrile
Eriobotrya japonica
B7VF77
pH 5.5
4877
101
2-naphthaldehyde
Eriobotrya japonica
B7VF77
pH 5.5
2374
148
benzaldehyde
Eriobotrya japonica
B7VF77
pH 5.5
146
9.6
Isobutyraldehyde
Eriobotrya japonica
B7VF77
pH 5.5
1646
50.8
p-anisaldehyde
Eriobotrya japonica
B7VF77
pH 5.5
8164
29.2
piperonal
Eriobotrya japonica
B7VF77
pH 5.5
13828
14.3
pivaldehyde
Eriobotrya japonica
B7VF77
pH 5.5
11149
19.4
propionaldehyde
Eriobotrya japonica
B7VF77
pH 5.5
273
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2 - 20
pH 5.0, 25C
9
(R)-HNL from crude extract, in 0.3 mM citrate buffer, at pH 5.0 and 25C
12.2
-
wild-type, 25C, pH 4.75
23.6
-
surface-modified mutant, 25C, pH 4.5
129
isoform HNL2 after purification, in 0.3 mM citrate buffer, at pH 5.0 and 25C; pH 5.0, 25C
133.6
-
wild-type, 25C, pH 6.0
220
(R)-HNL after 24.4fold purification, in 0.3 mM citrate buffer, at pH 5.0 and 25C
227
-
surface-modified mutant, 25C, pH 5.75
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2.5
-
at low pH very low amounts of crude enzyme catalyse stereoselective hydroxypivalaldehyde cyanohydrin formation in water based reaction systems
3.5 - 7
-
because of the base-catalyzed decomposition of mandelonitrile, pH dependence is only determined below pH 7.5. Activity increases from pH 3.5 to 6.2 and levels off between pH 6.2 and 7 for both isoforms
5
-
assay at
5 - 6
Prunus sp.
-
-
5.75
-
surface-modified mutant
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5
-
surface-modified mutant, less than 10% of maximum activity
4.5 - 6
pH 4.5: about 40% of maximal activity, pH 6.0: about 30% of maximal activity
4.75
-
wild-type, less than 10% of maximum activity
5
-
almost inactive below
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4
-
effect of buffer pH on the hydrocyanation of acetophenone
5
Prunus amygdalus turcomanica
-
carboligation reaction
15 - 25
-
reaction with benzaldehyde and HCN
25
Prunus pseudoarmeniaca
-
free and immobilized enzyme
30
-
assay at
35 - 40
-
-
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20 - 60
20C: about 50% of maximal activity, 60C: about 40% of maximal activity
50
Prunus pseudoarmeniaca
-
free enzyme retains about 57% of its maximum activity at 50C whereas immobilized enzymes onto Eupergit C and Eupergit C 250 L retain about 75 and 82% of their maximum activities, respectively, at 50C
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.1
-
isoelectric focusing, wild-type
5.3
-
isoelectric focusing
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
temporal and spatial expression patterns in flowers and mature seeds. Highest expression levels are detected during floral development. High level of expression in parenchymal cells, both in petals and in the style of the carpe
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
18000
-
gel filtration
55000 - 80000
Prunus sp.
-
-
57000
gel filtration; gel filtration
61000
-
electrospray ionisation mass spectrometry
72000
gel filtration
100000
Prunus amygdalus turcomanica
-
gel filtration
168000
-
isoenzyme A and C, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
the enzyme forms dimers in solution
monomer
multimer
-
x * 20000, SDS-PAGE
tetramer
Prunus amygdalus turcomanica
-
4 * 25000, SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
flavoprotein
enzyme shows a typical flavoprotein spectrum with absorption maxima at 389 nm nd 463 nm
glycoprotein
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
structure at a crystallographic resolution of 2.5 A and comparison with the S-selective HNL from Hevea brasiliensis. The structures exhibit an alpha/beta-hydrolase fold and a Ser-His-Asp catalytic triad. Modeling of complexes of the enzymes with both (R)- and (S)-mandelonitrile leads to a catalytic mechanism, in which His236 from the catalytic triad acts as a general base and the emerging negative charge on the cyano group is stabilized by main-chain amide groups and an alpha-helix dipole very similar to alpha/beta-hydrolases
-
to 2.5 A resolution, Structure exhibits a cupin fold, and manganese is bound to three histidine and one glutamine residue
3D structural data of the enzyme with the reaction product benzaldehyde bound within the active site, which allow unambiguous assignment of the location of substrate binding
-
hanging drop vapor diffusion using polyethylene glycol 4000 and isopropanol as coprecipitants. The crystals belong to the monoclinic space group P2(1) with unit cell parameters a = 69.9, b = 95.1, c = 95.6 A, and beta = 118.5 degrees. A complete set of diffraction data collected to 2.6 A resolution on native crystals of isoenzyme III
-
triclinic crystals grown in hanging drops, 1.5 A resolution, space group P1 with cell parameters a = 56.2 A, b = 67.5 A, c = 79.8
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3 - 9
60 min, stable
691375
4
Prunus pseudoarmeniaca
-
increasing the pH value above 4.0, the yield and ee are dramatically decreased due to the spontaneous chemical decomposition of the product
715946
4.75
-
wild-type, half-life 2.2 min, flavin-based fluorescent reporter fusion protein half-life 55-95 min
726741
5
-
20C, wild-type, half-life 0.16 h, surface-modified mutant, half-life 2.23 h
727311
5.4
-
half-life time: 2 h, the deactivation of the enzyme at slightly acidic pH is a result of pronounced structural unfolding
704762
6
-
20C, wild-type, half-life 60 h, surface-modified mutant, half-life 52.2 h
727311
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0 - 20
-
stable
0
-
pH 5.0, wild-type, half-life 18 min, surface-modified mutant, half-life 137 min
5 - 20
Prunus pseudoarmeniaca
-
free and immobilized enzyme preparations show optimal carboligation activity at 5C. As the temperature is increased from 5 to 20C, the yields decrease, however enantiomeric excess values (99%) unchange
25 - 50
Prunus pseudoarmeniaca
-
the half lives of free enzyme at 25 and 50C are 49.9 and 30.5 h, respectively and these correspondingly are 96.3 and 43.6 h for immobilized enzyme onto Eupergit C, and 138.6 and 50.2 h for immobilized enzyme onto Eupergit C 250 L
30
-
half-life time: 33 h
37
-
half-life 6.6 h; half-life time: 6.6 h
50
-
half-life 0.3 h; half-life time: 0.3 h
70
60 min, 68% residual activity
80
60 min, 28% residual activity
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
(R)-oxynitrilase immobilized as a cross-linked enzyme aggregate via precipitation with 1,2-dimethoxyethane and subsequent cross-linking using glutaraldehyde is stable and recyclable
-
both of immobilized enzymes (Eupergit C and Eupergit C250L) are used repeatedly 20times and the residual activities are about 97% of their initial activities
Prunus pseudoarmeniaca
-
the enzyme is stabilized by addition of sorbitol and saccharose
-
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
butyl acetate
-
synthesis of (R)-beta-nitro alcohols, highest enantioselectivity is obtained with n-butyl acetate as solvent with an optimum aqueous phase content of 50% (v/v)
dibutyl ether
diethyl ether
diisopropyl ether
Ethyl acetate
hexane
methyl-tert-butylether
additional information
-
effect of different organic solvents on the hydrocyanation of acetophenone tested
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4C, 20 mM potassium phosphate buffer, pH 6.0, stable for 30 d
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate precipitation
Prunus pseudoarmeniaca
-
ammonium sulfate precipitation and Ni Sepharose column chromatography
-
ammonium sulfate precipitation, DEAE Toyopearl column chromatography, phenyl Toyopearl column chromatography, and Superdex 200 gel filtration
partly, as crosslinked enzyme aggregates. Optimal conditions are initial glutaraldehyde concentration of 25% w/v, ammonium sulfate saturation concentration of 43% w/v, and crosslinking time of 18 h
-
recombinant enzyme
-
to homogeneity. The final yield, of 36% with 49fold purification, is obtained by 30-80% (NH4)2SO4 fractionation and column chromatography on DEAE-Toyopearl and concanavalin A Sepharose 4B, which suggests the presence of a carbohydrate side chain
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloned and sequenced
-
expresion in Pichia pastoris; expressed in Pichia pastoris strain GS115
expressed in Escherichia coli BL21(DE3) cells
-
expressed in Pichia pastoris
-
expression in Escherichia coli
-
expression of mutant and wild-type enzymes in Pichia pastoris X33
-
overexpressed in Pichia pastoris
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D208N
-
less than 2% residual activity
H236F
-
less than 2% residual activity
M237K
-
no residual activity
M237L
-
100% residual activity
N12T
-
less than 2% residual activity
N12T/M237K
-
expression results in insoluble protein
S81A
-
less than 2% residual activity
H459N
-
less than 5% of the activity compared to wild type
H497N
-
less than 5% of the activity compared to wild type
I108M/A111G
-
mutant with improved catalytic properties: recovery of a 89.9% yield of (R)-2-chloromandelonitrile with an enantiomeric excess of 97.6% enantiomeric excess, about 4% residual aldehyde. The mutant also contains two silent mutations at position 85 and position 432
L1Q
-
mutation enhances expression in Pichia pastoris
L1Q/A111G
-
activity is similar to wild-type enzyme with its preferred substrate benzaldehyde. Directed evolution of PaHNL5/L1Q/A11G
L1Q/N3I/I108M/A111G
-
mutant with improved catalytic properties: recovery of a 92.7% yield of (R)-2-chloromandelonitrile with an ee of 98.6% enantiomeric excess, about 2% residual aldehyde, the mutant also contains two silent mutations at position 85 and position 432
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis