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Literature summary for 4.2.1.84 extracted from

  • Black, G.; Gregson, T.; McPake, C.; Perry, J.; Zhang, M.
    Biotransformation of nitriles using the solvent-tolerant nitrile hydratase from Rhodopseudomonas palustris CGA009 (2010), Tetrahedron Lett., 51, 1639-1641.
No PubMed abstract available

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli BL21(DE3) cells Rhodopseudomonas palustris

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Rhodopseudomonas palustris the nitrile hydratase can hydrate aliphatic, aromatic and heterocyclic nitriles under very mild conditions, in mixtures of pH 7 buffer and a range of organic solvents, often with excellent chemoselectivity. Major determinant of hydration occurring is the degree of steric hindrance around the nitrile moiety and/or size of the substrates ?
-
?
additional information Rhodopseudomonas palustris CGA009 the nitrile hydratase can hydrate aliphatic, aromatic and heterocyclic nitriles under very mild conditions, in mixtures of pH 7 buffer and a range of organic solvents, often with excellent chemoselectivity. Major determinant of hydration occurring is the degree of steric hindrance around the nitrile moiety and/or size of the substrates ?
-
?

Organism

Organism UniProt Comment Textmining
Rhodopseudomonas palustris
-
-
-
Rhodopseudomonas palustris CGA009
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2,6-difluorobenzonitrile + H2O
-
Rhodopseudomonas palustris 2,6-difluorobenzamide
-
?
2,6-difluorobenzonitrile + H2O
-
Rhodopseudomonas palustris CGA009 2,6-difluorobenzamide
-
?
2-bromobenzonitrile + H2O
-
Rhodopseudomonas palustris 2-bromobenzamide
-
ir
2-chlorobenzonitrile + H2O
-
Rhodopseudomonas palustris 2-chlorobenzamide
-
ir
2-fluorobenzonitrile + H2O
-
Rhodopseudomonas palustris 2-fluorobenzamide
-
ir
2-methoxybenzonitrile + H2O
-
Rhodopseudomonas palustris 2-methoxybenzamide
-
ir
2-methylbenzonitrile + H2O
-
Rhodopseudomonas palustris 2-methylbenzamide
-
ir
3-(trifluoromethyl)benzonitrile + H2O 5% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 3-(trifluoromethyl)benzamide
-
?
3-(trifluoromethyl)benzonitrile + H2O 5% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris CGA009 3-(trifluoromethyl)benzamide
-
?
3-(trifluoromethyl)pyridine-4-carbonitrile + H2O
-
Rhodopseudomonas palustris 3-(trifluoromethyl)pyridine-4-carboxamide
-
ir
3-bromobenzonitrile + H2O 5% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 3-bromobenzamide
-
?
3-chlorobenzonitrile + H2O 95% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 3-chlorobenzamide
-
?
3-fluorobenzonitrile + H2O above 99.9% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 3-fluorobenzamide
-
?
3-methoxybenzonitrile + H2O 3% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 3-methoxybenzamide
-
?
3-methylbenzonitrile + H2O 17% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 3-methylbenzamide
-
?
3-phenylpropanenitrile + H2O 99.9% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 3-phenylpropanamide
-
ir
4-(trifluoromethyl)benzonitrile + H2O above 99.9% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 4-(trifluoromethyl)benzamide
-
ir
4-acetylbenzonitrile + H2O above 99% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 4-acetylbenzamide
-
ir
4-bromobenzonitrile + H2O
-
Rhodopseudomonas palustris 4-bromobenzamide
-
ir
4-bromobenzonitrile + H2O above 99% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 4-bromobenzamide
-
?
4-chlorobenzonitrile + H2O above 99.9% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 4-chlorobenzamide
-
?
4-chlorobenzonitrile + H2O
-
Rhodopseudomonas palustris 4-chlorbenzamide
-
ir
4-fluorobenzonitrile + H2O above 99.9% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 4-fluorobenzamide
-
?
4-fluorobenzonitrile + H2O
-
Rhodopseudomonas palustris 4-fluorbenzamide
-
ir
4-hydroxybenzonitrile + H2O
-
Rhodopseudomonas palustris 4-hydroxybenzoic acid amide
-
?
4-hydroxybenzonitrile + H2O
-
Rhodopseudomonas palustris CGA009 4-hydroxybenzoic acid amide
-
?
4-hydroxybenzonitrile + H2O
-
Rhodopseudomonas palustris 4-hydroxybenzamide
-
?
4-methoxybenzonitrile + H2O above 99% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 4-methoxybenzamide
-
ir
4-methylbenzonitrile + H2O above 99.9% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 4-methylbenzamide
-
ir
benzonitrile + H2O 99.9% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris benzamide
-
ir
benzonitrile + H2O 99.9% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris CGA009 benzamide
-
ir
ethyl 2-cyanobenzoate + H2O
-
Rhodopseudomonas palustris ethyl 2-carbamoylbenzoate
-
ir
ethyl 3-cyanobenzoate + H2O no conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris ethyl 3-carbamoylbenzoate
-
?
ethyl 4-cyanobenzoate + H2O 95% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris ethyl 4-carbamoylbenzoate
-
ir
furan-2-carbonitrile + H2O 99.9% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris furan-2-carboxamide
-
ir
methyl 4-cyanobenzoate + H2O 98% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris methyl 4-carbamoylbenzoate
-
ir
additional information the nitrile hydratase can hydrate aliphatic, aromatic and heterocyclic nitriles under very mild conditions, in mixtures of pH 7 buffer and a range of organic solvents, often with excellent chemoselectivity. Major determinant of hydration occurring is the degree of steric hindrance around the nitrile moiety and/or size of the substrates Rhodopseudomonas palustris ?
-
?
additional information the nitrile hydratase can hydrate aliphatic, aromatic and heterocyclic nitriles under very mild conditions, in mixtures of pH 7 buffer and a range of organic solvents, often with excellent chemoselectivity. Major determinant of hydration occurring is the degree of steric hindrance around the nitrile moiety and/or size of the substrates Rhodopseudomonas palustris CGA009 ?
-
?
phenylacetonitrile + H2O 28% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 2-phenylacetamide
-
ir
pyridine-2-carbonitrile + H2O 99.9% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris pyridine-2-carboxamide
-
ir
pyridine-4-carbonitrile + H2O 99.9% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris pyridine-4-carboxamide
-
ir
thiophen-2-ylacetonitrile + H2O 89% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris 2-(thiophen-2-yl)acetamide
-
ir
thiophene-2-carbonitrile + H2O 99.9% conversion, in phosphate buffer pH 7.0, at 30°C Rhodopseudomonas palustris thiophene-2-carboxamide
-
?
thiophene-2-carbonitrile + H2O
-
Rhodopseudomonas palustris thiophen-2-carboxamide
-
ir

Synonyms

Synonyms Comment Organism
NHase
-
Rhodopseudomonas palustris

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
assay at Rhodopseudomonas palustris

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7
-
assay at Rhodopseudomonas palustris