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(R)-mandelonitrile + H2O
(R)-mandelamide
wild-type enzyme catalyzes the conversion of rac-mandelonitrile to (S)-mandelamide with an enantiomeric excess of 52.6%
-
-
?
(S)-mandelonitrile + H2O
(S)-mandelamide
wild-type enzyme catalyzes the conversion of rac-mandelonitrile to (S)-mandelamide with an enantiomeric excess of 52.6%
-
-
?
1-naphthylnitrile + H2O
1-naphthylamide
-
-
-
-
?
2,2-dimethylcyclopropanecarbonitrile + H2O
2,2-dimethylcyclopropanecarboxamide
-
-
-
-
?
2-cyanobenzamide + H2O
benzene-1,2-dicarboxamide
-
-
-
?
2-cyanopyridine + H2O
pyridine-2-carbamide
-
-
-
-
?
2-furonitrile + H2O
2-furoamide
-
-
-
-
?
2-naphthylacetonitrile + H2O
2-naphthylacetamide
-
-
-
-
?
3-cyanopyridine + H2O
nicotinamide
3-cyanopyridine + H2O
pyridine-3-carbamide
4-cyanobenzamide + H2O
benzene-1,4-dicarboxamide
-
-
-
?
4-cyanopyridine + H2O
isonicotinamide
-
-
-
-
?
5-cyanovaleramide
adiponitrile + H2O
-
-
-
r
5-hydroxymethyl-2-furonitrile + H2O
5-hydroxymethyl-2-furamide
-
-
-
-
?
acetonitrile + H2O
acetamide
acrylamide + H2O
acrylonitrile
-
-
-
-
?
acrylonitrile + H2O
2-propenoic acid amide
acrylonitrile + H2O
acrylamide
-
-
-
-
?
adiponitrile + 2 H2O
adipic acid amide
wild-type enzyme forms only adipamide after a 4 h reaction. Y68T and W72Y mutations cause a significant shift in product formation and form primarily 5-cyanovaleramide. Mutant enzyme Y68T/W72Y produces 100% 5-cyanovaleramide
-
-
?
adiponitrile + H2O
5-cyanovaleramide
wild-type enzyme forms only adipamide after a 4 h reaction. Y68T and W72Y mutations cause a significant shift in product formation and form primarily 5-cyanovaleramide. Mutant enzyme Y68T/W72Y produces 100% 5-cyanovaleramide
-
-
r
benzonitrile + H2O
benzamide
-
-
-
-
?
benzonitrile + H2O
benzoic acid amide
-
-
-
-
?
bromoxynil + H2O
?
-
-
-
-
?
chloroacetonitrile + H2O
chloroacetamide
-
-
-
-
?
chloroxynil acid + H2O
?
-
-
-
-
?
chloroxynil amide + H2O
?
-
-
-
-
?
crotononitrile + H2O
(E)-2-butenoic acid amide
cyanoacetamide
malononitrile + H2O
-
-
-
r
cyanopyrazine + H2O
pyrazincarbamide
-
-
-
-
?
cyclopropylcyanide + H2O
?
-
-
-
-
?
dichlobenil amide + H2O
?
-
-
-
-
?
ethylene cyanhydrine + H2O
?
-
-
-
-
?
ioxynil acid + H2O
?
-
-
-
-
?
isobutyronitrile + H2O
isobutyramide
-
-
-
-
?
malononitrile + 2 H2O
malonamide
the use of the wild-type enzyme leads to malonamide formation with 97.3% malononitrile conversion. Variants Y68T and W72Y show a drastic change in regiospecificity by producing mainly the omega-cyanocarboxamide, cyanoacetamide, at a relatively low malononitrile conversion. Mutant enzyme Y68T/W72Y produces 97.1% omega-cyanocarboxamide
-
-
?
malononitrile + H2O
cyanoacetamide
the use of the wild-type enzyme leads to malonamide formation with 97.3% malononitrile conversion. Variants Y68T and W72Y show a drastic change in regiospecificity by producing mainly the omega-cyanocarboxamide, cyanoacetamide, at a relatively low malononitrile conversion. Mutant enzyme Y68T/W72Y produces 97.1% omega-cyanocarboxamide
-
-
r
methacrylonitrile + H2O
methylacrylic acid amide
-
-
-
-
?
n-butyronitrile + H2O
n-butyric acid amide
-
-
-
-
?
phthalodinitrile + 2 H2O
phthalamide
the wild-type enzyme forms 100% phthalamide from phthalodinitrile. The mutant enzymes Y68T and W72Y result in a higher 2-cyanobenzamide formation than their parent enzyme. Mutant enzyme Y68T/W72Y produces 100% 2-cyanobenzamide from phthalodinitrile
-
-
?
phthalodinitrile + H2O
2-cyanobenzamide
the wild-type enzyme forms 100% phthalamide from phthalodinitrile. The mutant enzymes Y68T and W72Y result in a higher 2-cyanobenzamide formation than their parent enzyme. Mutant enzyme Y68T/W72Y produces 100% 2-cyanobenzamide from phthalodinitrile
-
-
?
propionitrile + H2O
propionic acid amide
terephthalonitrile + 2 H2O
terephthalamide
the wild-type enzyme prefers terephthalonitrile to catalyze mainly into terephthalamide (84.3%) with a conversion up to 99.2 %. Variants Y68T and W72Y show a change in regiospecificity by producing mainly the 4-cyanobenzamide. Mutant enzyme Y68T/W72Y produces 98.2% 4-cyanobenzamide from terephthalonitrile
-
-
?
terephthalonitrile + H2O
4-cyanobenzamide
the wild-type enzyme prefers terephthalonitrile to catalyze mainly into terephthalamide (84.3%) with a conversion up to 99.2 %. Variants Y68T and W72Y show a change in regiospecificity by producing mainly the 4-cyanobenzamide. Mutant enzyme Y68T/W72Y produces 98.2% 4-cyanobenzamide from terephthalonitrile
-
-
?
trans-cinnamonitrile + H2O
trans-cinnamide
-
-
-
-
?
additional information
?
-
3-cyanopyridine + H2O
nicotinamide
-
-
-
-
?
3-cyanopyridine + H2O
nicotinamide
-
H-NHase activity
-
-
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
-
-
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
-
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
i.e. nicotinamide
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
i.e. nicotinamide
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
i.e. nicotinamide
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
i.e. nicotinamide
?
acetonitrile + H2O
acetamide
-
-
-
-
?
acetonitrile + H2O
acetamide
-
best substrate
-
-
?
acrylonitrile + H2O
2-propenoic acid amide
-
-
-
-
?
acrylonitrile + H2O
2-propenoic acid amide
-
-
i.e. acrylic acid amide
?
crotononitrile + H2O
(E)-2-butenoic acid amide
-
-
-
-
?
crotononitrile + H2O
(E)-2-butenoic acid amide
-
19% of the activity with propionitrile
-
-
?
propionitrile + H2O
propionic acid amide
-
-
-
-
?
propionitrile + H2O
propionic acid amide
-
10% of conversion in 24 h
i.e. propionamide
?
additional information
?
-
-
specificity overview
-
-
?
additional information
?
-
-
H-NHase acts preferentially on aliphatic nitriles, while L-NHase has a higher affinity for aromatic nitriles
-
-
?
additional information
?
-
-
NhhG forms a complex with the alpha-subunit of H-NHase. NhhAG is very similar to the mediator of L-NHase, NhlAE, which is a heterotrimer complex consisting of the cobalt-containing alpha-subunit of L-NHase and NhlE
-
-
?
additional information
?
-
-
no activity with 2,6-dichlorobenzamide and dichlobenil acid
-
-
?
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Kobayashi, M.; Nishiyama, M.; Nagasawa, T.; Horinouchi, S.; Beppu, T.; Yamada, H.
Cloning, nucleotide sequence and expression in Escherichia coli of two cobalt-containing nitrile hydratase genes from Rhodococcus rhodochrous J1
Biochim. Biophys. Acta
1129
23-33
1991
Rhodococcus rhodochrous, Rhodococcus rhodochrous J1, Rhodococcus sp., Rhodococcus sp. N-774
brenda
Nagasawa, T.; Takeuchi, K.; Yamada, H.
Occurrence of a cobalt-induced and cobalt-containing nitrile hydratase in Rhodococcus rhodochrous J1
Biochem. Biophys. Res. Commun.
155
1008-1016
1988
Pseudomonas chlororaphis, Rhodococcus rhodochrous, Rhodococcus rhodochrous J1
brenda
Duran, R.; Chion, C.K.N.C.K.; Bigey, F.; Arnaud, A.; Galzy, P.
The N-terminal amino acid sequences of Brevibacterium sp. R312 nitrile hydratase
J. Basic Microbiol.
32
13-19
1992
Arthrobacter sp., Brevibacterium sp., Brevibacterium sp. R312, Corynebacterium sp., Pseudomonas chlororaphis, Rhodococcus rhodochrous, Rhodococcus rhodochrous J1, Rhodococcus sp., Rhodococcus sp. 7, Rhodococcus sp. N-774
brenda
Nagasawa, T.; Takeuchi, K.; Yamada, H.
Characterization of a new cobalt-containing nitrile hydratase purified from urea-induced cells of Rhodococcus rhodochrous J1
Eur. J. Biochem.
196
581-589
1991
Rhodococcus rhodochrous, Rhodococcus rhodochrous J1
brenda
Yamada, H.; Kobayashi, M.
Nitrile hydratase and its application to industrial production of acrylamide
Biosci. Biotechnol. Biochem.
60
1391-1400
1996
Agrobacterium tumefaciens, Albifimbria verrucaria, Arthrobacter sp., Pseudomonas chlororaphis, Pseudomonas chlororaphis B23, Rhodococcus rhodochrous, Rhodococcus rhodochrous J1, Rhodococcus sp.
brenda
Kaufmann, G.; Dautzenberg, H.; Henkel, H.; Mller, G.; Schfer, T.; Undeutsch, B.; Oettel, M.
Nitrile hydratase from Rhodococcus erythropolis: metabolization of steroidal compounds with a nitrile group
Steroids
64
535-540
1999
Rhodococcus erythropolis, Rhodococcus rhodochrous
brenda
Wieser, M.; Takeuchi, K.; Wada, Y.; Yamada, H.; Nagasawa, T.
Low-molecular-mass nitrile hydratase from Rhodococcus rhodochrous J1: purification, substrate specificity and comparison with the analogous high-molecular-mass enzyme
FEMS Microbiol. Lett.
169
17-22
1998
Rhodococcus rhodochrous, Rhodococcus rhodochrous J1
-
brenda
Kobayashi, M.; Shimizu, S.
Metalloenzyme nitrile hydratase: structure, regulation, and application to biotechnology
Nat. Biotechnol.
16
733-736
1998
Pseudomonas chlororaphis, Pseudomonas chlororaphis B23, Pseudomonas putida, Rhodococcus rhodochrous, Rhodococcus rhodochrous J1, Rhodococcus sp., Rhodococcus sp. N-774, Rhodococcus sp. R312
brenda
Tauber, M.M.; Cavaco-Paulo, A.; Robra, K.; Gubitz, G.M.
Nitrile hydratase and amidase from Rhodococcus rhodochrous hydrolyze acrylic fibers and granular polyacrylonitriles
Appl. Environ. Microbiol.
66
1634-1638
2000
Rhodococcus rhodochrous, Rhodococcus rhodochrous NCIMB 11216
brenda
Petersen, M.; Kiener, A.
Biocatalysis - Preparation and functionalization of N-heterocycles
Green Chem.
4
99-106
1999
Rhodococcus rhodochrous, Rhodococcus rhodochrous J1
-
brenda
Kashiwagi, M.; Fuhshuku, K.I.; Sugai, T.
Control of the nitrile-hydrolyzing enzyme activity in Rhodococcus rhodochrous IFO 15564: preferential action of nitrile hydratase and amidase depending on the reaction condition factors and its application to the one-pot preparation of amides from aldehydes
J. Mol. Catal. B
29
249-258
2004
Rhodococcus rhodochrous, Rhodococcus rhodochrous IFO 15564
-
brenda
Yeom, S.; Kim, H.; Oh, D.
Enantioselective production of 2,2-dimethylcyclopropane carboxylic acid from 2,2-dimethylcyclopropane carbonitrile using the nitrile hydratase and amidase of Rhodococcus erythropolis ATCC 25544
Enzyme Microb. Technol.
41
842-848
2007
Rhodococcus erythropolis, Rhodococcus rhodochrous, Nocardia transvalensis, Comamonas oleophilus
-
brenda
Prasad, S.; Raj, J.; Bhalla, T.
Purification of a hyperactive nitrile hydratase from resting cells of Rhodococcus rhodochrous PA-34
Indian J. Microbiol.
49
237-242
2009
Rhodococcus rhodochrous, Rhodococcus rhodochrous PA-34
brenda
Zhou, Z.; Hashimoto, Y.; Cui, T.; Washizawa, Y.; Mino, H.; Kobayashi, M.
Unique biogenesis of high-molecular mass multimeric metalloenzyme nitrile hydratase: intermediates and a proposed mechanism for self-subunit swapping maturation
Biochemistry
49
9638-9648
2010
Rhodococcus rhodochrous, Rhodococcus rhodochrous J1
brenda
Vesela, A.B.; Pelantova, H.; Sulc, M.; Mackova, M.; Lovecka, P.; Thimova, M.; Pasquarelli, F.; Picmanova, M.; Patek, M.; Bhalla, T.C.; Martinkova, L.
Biotransformation of benzonitrile herbicides via the nitrile hydratase-amidase pathway in Rhodococci
J. Ind. Microbiol. Biotechnol.
39
1811-1819
2012
Rhodococcus erythropolis, Rhodococcus rhodochrous, Rhodococcus erythropolis A4, Rhodococcus rhodochrous PA-34
brenda
Kang, M.S.; Han, S.S.; Kim, M.Y.; Kim, B.Y.; Huh, J.P.; Kim, H.S.; Lee, J.H.
High-level expression in Corynebacterium glutamicum of nitrile hydratase from Rhodococcus rhodochrous for acrylamide production
Appl. Microbiol. Biotechnol.
98
4379-4387
2014
Rhodococcus rhodochrous, Rhodococcus rhodochrous M33
brenda
Cheng, Z.; Peplowski, L.; Cui, W.; Xia, Y.; Liu, Z.; Zhang, J.; Kobayashi, M.; Zhou, Z.
Identification of key residues modulating the stereoselectivity of nitrile hydratase toward rac-mandelonitrile by semi-rational engineering
Biotechnol. Bioeng.
115
524-535
2018
Rhodococcus rhodochrous (P29378 AND P29379), Rhodococcus rhodochrous J1 (P29378 AND P29379)
brenda
Cheng, Z.; Cui, W.; Xia, Y.; Peplowski, L.; Kobayashi, M.; Zhou, Z.
Modulation of nitrile hydratase regioselectivity towards dinitriles by tailoring the substrate binding pocket residues
ChemCatChem
10
449-458
2018
Rhodococcus rhodochrous (P29378 AND P29379), Rhodococcus rhodochrous J1 (P29378 AND P29379)
-
brenda
Lan, Y.; Zhang, X.; Liu, Z.; Zhou, L.; Shen, R.; Zhong, X.; Cui, W.; Zhou, Z.
Overexpression and characterization of two types of nitrile hydratases from Rhodococcus rhodochrous J1
PLoS ONE
12
e0179833
2017
Rhodococcus rhodochrous (P21219 AND P21220), Rhodococcus rhodochrous (P29378 AND P29379), Rhodococcus rhodochrous, Rhodococcus rhodochrous J1 (P21219 AND P21220), Rhodococcus rhodochrous J1 (P29378 AND P29379), Rhodococcus rhodochrous J1
brenda