Biotransformation of heterocyclic dinitriles by Rhodococcus erythropolis and fungal nitrilases.
2,6-Pyridinedicarbonitrile (1a) and 2,4-pyridinedicarbonitrile (2a) were hydrated by Rhodococcus erythropolis A4 to 6-cyanopyridine-2-carboxamide (1b; 83% yield) and 2-cyanopyridine-4-carboxamide (2b; 97% yield), respectively, after 10 min. After 118 h, the intermediates 1b or 2b were transformed into 2,6-pyridinedicarboxamide (1c; 35% yield) and 2,6-pyridinedicarboxylic acid (1d; 60% yield) or 2-cyanopyridine-4-carboxylic acid (2c; 64% yield), respectively. The nitrilase from Fusarium solani afforded cyanocarboxylic acids 1e and 2c after 118 h (yields 95 and 62%, respectively). 3,4-Pyridinedicarbonitrile (3a) and 2,3-pyrazinedicarbonitrile (4a) were inferior substrates of nitrile hydratase and nitrilase.
Vejvoda
Vojtech
V
Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeská 1083, CZ-142 20, Prague 4, Czech Republic.
Sveda
Ondrej
O
Kaplan
Ondrej
O
Prikrylová
Vera
V
Elisáková
Veronika
V
Himl
Michal
M
Kubác
David
D
Pelantová
Helena
H
Kuzma
Marek
M
Kren
Vladimír
V
Martínková
Ludmila
L
D000577:Amides / Q000378:metabolism; D000619:Aminohydrolases / Q000378:metabolism*; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D005658:Fungi / Q000201:enzymology*; D006571:Heterocyclic Compounds / Q000737:chemistry / Q000378:metabolism*; D006868:Hydrolysis; D009570:Nitriles / Q000737:chemistry / Q000378:metabolism*; D012240:Rhodococcus / Q000201:enzymology*; D013379:Substrate Specificity
D000577:Amides; D006571:Heterocyclic Compounds; D009570:Nitriles; D000619:Aminohydrolases; C021867:nitrilase