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(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
?
cyanide + (2E)-hex-2-enal
(3E)-2-hydroxyhept-3-enenitrile
-
53% enantiomeric excess
-
?
cyanide + 2-bromobenzaldehyde
(2R)-(2-bromophenyl)(hydroxy)ethanenitrile
-
98% enantiomeric excess
-
?
cyanide + 2-chlorobenzaldehyde
(2R)-(2-chlorophenyl)(hydroxy)ethanenitrile
-
99% enantiomeric excess
-
?
cyanide + 2-fluorobenzaldehyde
(2R)-(2-fluorophenyl)(hydroxy)ethanenitrile
-
99% enantiomeric excess
-
?
cyanide + 2-iodobenzaldehyde
(2R)-(2-iodophenyl)(hydroxy)ethanenitrile
-
more than 95% enantiomeric excess
-
?
cyanide + 3-bromobenzaldehyde
(2R)-(3-bromophenyl)(hydroxy)ethanenitrile
-
95% enantiomeric excess
-
?
cyanide + 3-chlorobenzaldehyde
(2R)-(3-chlorophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
cyanide + 3-fluorobenzaldehyde
(2R)-(3-fluorophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
cyanide + 3-iodobenzaldehyde
(2R)-(3-iodophenyl)(hydroxy)ethanenitrile
-
93% enantiomeric excess
-
?
cyanide + 3-phenoxybenzaldehyde
(2R)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
-
more than 95% enantiomeric excess
-
?
cyanide + 3-phenylpropanal
(2R)-2-hydroxy-4-phenylbutanenitrile
-
68% enantiomeric excess
-
?
cyanide + 4-bromobenzaldehyde
(2R)-(4-bromophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
cyanide + 4-chlorobenzaldehyde
(2R)-(4-chlorophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
cyanide + 4-fluorobenzaldehyde
(2R)-(4-fluorophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
cyanide + 4-hydroxybenzaldehyde
(2R)-(4-hydroxyphenyl)(hydroxy)ethanenitrile
-
97% enantiomeric excess
-
?
cyanide + 4-iodobenzaldehyde
(2R)-(4-iodophenyl)(hydroxy)ethanenitrile
-
92% enantiomeric excess
-
?
cyanide + 4-methoxybenzaldehyde
(2R)-(4-methoxyphenyl)(hydroxy)ethanenitrile
-
68% enantiomeric excess
-
?
cyanide + 6-methylhept-5-en-2-one
(2R)-2-hydroxy-2,6-dimethylhept-5-enenitrile
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
more than 99% enantiomeric excess
-
?
cyanide + cyclohexanone
1-hydroxycyclohexanecarbonitrile
-
-
-
?
cyanide + decanal
(2R)-2-hydroxyundecanal
-
56% enantiomeric excess
-
?
cyanide + hexan-2-one
(2R)-2-hydroxy-2-methylhexanenitrile
-
95% enantiomeric excess
-
?
cyanide + hexanal
(2R)-2-hydroxyheptanenitrile
-
98% enantiomeric excess
-
?
cyanide + phenylacetaldehyde
(2R)-2-hydroxy-3-phenylpropanenitrile
-
96% enantiomeric excess
-
?
cyanide + thiophene-2-carbaldehyde
hydroxy(thiophen-2-yl)ethanenitrile
-
separation of enantiomers not posible
-
?
HCN + 2-chlorobenzaldehyde
(R)-2-hydroxy-2-(2-chlorophenyl)acetonitrile
-
-
-
?
HCN + benzaldehyde
(R)-2-hydroxy-2-phenylacetonitrile
-
-
-
?
nitromethane + 2-chlorobenzaldehyde
(1R)-1-(2-chlorophenyl)-2-nitroethanol
-
34% yield, 68% enantiomeric excess
-
?
nitromethane + 3-methoxybenzaldehyde
(1R)-1-(3-methoxyphenyl)-2-nitroethanol
-
17% yield, 91% enantiomeric excess
-
?
nitromethane + 4-fluorobenzaldehyde
(1R)-1-(4-fluorophenyl)-2-nitroethanol
-
20% yield, 81% enantiomeric excess
-
?
nitromethane + benzaldehyde
(1R)-2-nitro-1-phenylethanol
30% yield, 91% enantiomeric excess
-
-
?
(R)-4-hydroxymandelonitrile
cyanide + 4-hydroxybenzaldehyde
-
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
2-chlorobenzaldehyde + nitromethane
1-(2-chlorophenyl)-2-nitroethanol
-
34% yield after 2 h
-
?
2-methoxybenzaldehyde + nitromethane
1-(2-methoxyphenyl)-2-nitroethanol
-
13% yield after 2 h
-
?
2-methylbenzaldehyde + nitromethane
1-(2-methylphenyl)-2-nitroethanol
-
12% yield after 2 h
-
?
3-(2-naphthyl)benzaldehyde + nitromethane
(1R)-1-[3-(naphthalen-2-yl)phenyl]-2-nitroethanol
-
7% yield after 2 h
-
?
3-chlorobenzaldehyde + nitromethane
1-(3-chlorophenyl)-2-nitroethanol
-
17% yield after 2 h
-
?
3-methoxybenzaldehyde + nitromethane
1-(3-methoxyphenyl)-2-nitroethanol
-
17% yield after 2 h
-
?
3-methylbenzaldehyde + nitromethane
1-(3-methylphenyl)-2-nitroethanol
-
12% yield after 2 h
-
?
4-bromobenzaldehyde + nitromethane
1-(4-bromophenyl)-2-nitroethanol
-
20% yield after 2 h
-
?
4-chlorobenzaldehyde + nitromethane
1-(4-chlorophenyl)-2-nitroethanol
-
9% yield after 2 h
-
?
4-fluorobenzaldehyde + nitromethane
1-(4-fluorophenyl)-2-nitroethanol
-
9% yield after 2 h
-
?
4-methoxybenzaldehyde + nitromethane
1-(4-methoxyphenyl)-2-nitroethanol
-
2% yield after 2 h
-
?
4-methylbenzaldehyde + nitromethane
1-(4-methylphenyl)-2-nitroethanol
-
11% yield after 2 h
-
?
benzaldehyde + nitromethane
(R)-2-nitro-1-phenylethanol
-
30% yield after 2 h
-
?
cyanide + 4-hydroxybenzaldehyde
(R)-4-hydroxymandelonitrile
-
-
-
-
r
additional information
?
-
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
?
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
-
r
additional information
?
-
broad substrate range includes alphatic and aromatic aldehydes as well as ketones. Low activity with acetaldehyde, propionaldehyde and acetone cyanohydrin
-
-
?
additional information
?
-
-
broad substrate range includes alphatic and aromatic aldehydes as well as ketones. Low activity with acetaldehyde, propionaldehyde and acetone cyanohydrin
-
-
?
additional information
?
-
-
low activity towards acetone cyanohydrin
-
-
?
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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
additional information
design of a surface-modified variant incorporating 11 changes in the amino acids on the protein surface to stabilze the protein at acidic pH. Mutant shows a broadened pH optimum towards the acidic range, along with enhancement of activity by up to twofold and significantly increased pH- and thermostabilities. The effect is probably due to a shift of the isoelectic point from pH 5.1 to 4.8. Mutant is applicable in aqueous/organic two-phase systems
additional information
-
design of a surface-modified variant incorporating 11 changes in the amino acids on the protein surface to stabilze the protein at acidic pH. Mutant shows a broadened pH optimum towards the acidic range, along with enhancement of activity by up to twofold and significantly increased pH- and thermostabilities. The effect is probably due to a shift of the isoelectic point from pH 5.1 to 4.8. Mutant is applicable in aqueous/organic two-phase systems
additional information
fusion of enzyme to different fluorescent reporter proteins. All fusion constructs retain enzymatic activity and fluorescence in vivo and in vitro, but show significant differences in activity and pH stability. Flavin-based fluorescent reporter fusions show almost 2 orders of magnitude-increased half-lives in the weakly acidic pH range compared to findings for the wild-type enzyme. This increased stability is apparently caused by oligomerization mediated via the flavin-based tag. The increased stability of the fusion proteins enables the efficient synthesis of (R)-mandelonitrile in an aqueous-organic two-phase system at a pH below 5
additional information
-
fusion of enzyme to different fluorescent reporter proteins. All fusion constructs retain enzymatic activity and fluorescence in vivo and in vitro, but show significant differences in activity and pH stability. Flavin-based fluorescent reporter fusions show almost 2 orders of magnitude-increased half-lives in the weakly acidic pH range compared to findings for the wild-type enzyme. This increased stability is apparently caused by oligomerization mediated via the flavin-based tag. The increased stability of the fusion proteins enables the efficient synthesis of (R)-mandelonitrile in an aqueous-organic two-phase system at a pH below 5
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Andexer, J.; von Langermann, J.; Mell, A.; Bocola, M.; Kragl, U.; Eggert, T.; Pohl, M.
An R-selective hydroxynitrile lyase from Arabidopsis thaliana with an alpha/beta-hydrolase fold
Angew. Chem. Int. Ed. Engl.
46
8679-8681
2007
Arabidopsis thaliana (Q9LFT6), Arabidopsis thaliana
brenda
Guterl, J.K.
Andexer, J.N.; Sehl, T.; von Langermann, J.; Frindi-Wosch, I.; Rosenkranz, T.; Fitter, J.; Gruber, K.; Kragl, U.; Eggert, T.; Pohl, M.: Uneven twins: comparison of two enantiocomplementary hydroxynitrile lyases with alpha/beta-hydrolase fold
J. Biotechnol.
141
166-173
2009
Arabidopsis thaliana
brenda
Fuhshuku, K.; Asano, Y.
Synthesis of (R)-beta-nitro alcohols catalyzed by R-selective hydroxynitrile lyase from Arabidopsis thaliana in the aqueous-organic biphasic system
J. Biotechnol.
153
153-159
2011
Arabidopsis thaliana, Arabidopsis thaliana (Q9LFT6)
brenda
Scholz, K.E.; Kopka, B.; Wirtz, A.; Pohl, M.; Jaeger, K.E.; Krauss, U.
Fusion of a flavin-based fluorescent protein to hydroxynitrile lyase from Arabidopsis thaliana improves enzyme stability
Appl. Environ. Microbiol.
79
4727-4733
2013
Arabidopsis thaliana (Q9LFT6), Arabidopsis thaliana
brenda
Andexer, J.N.; Staunig, N.; Eggert, T.; Kratky, C.; Pohl, M.; Gruber, K.
Hydroxynitrile lyases with alpha/beta-hydrolase fold: two enzymes with almost identical 3D structures but opposite enantioselectivities and different reaction mechanisms
ChemBioChem
13
1932-1939
2012
Arabidopsis thaliana (Q9LFT6), Arabidopsis thaliana
brenda
Okrob, D.; Metzner, J.; Wiechert, W.; Gruber, K.; Pohl, M.
Tailoring a stabilized variant of hydroxynitrile lyase from Arabidopsis thaliana
ChemBioChem
13
797-802
2012
Arabidopsis thaliana (Q9LFT6), Arabidopsis thaliana
brenda
Kopka, B.; Diener, M.; Wirtz, A.; Pohl, M.; Jaeger, K.E.; Krauss, U.
Purification and simultaneous immobilization of Arabidopsis thaliana hydroxynitrile lyase using a family 2 carbohydrate-binding module
Biotechnol. J.
10
811-819
2015
Arabidopsis thaliana (Q9LFT6)
brenda