title: Biotransformation of heterocyclic dinitriles by Rhodococcus erythropolis and fungal nitrilases.
abstract: 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.
authors.affiliation: Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeská 1083, CZ-142 20, Prague 4, Czech Republic.
authors.forename: Vojtech
authors.initials: V
authors.lastname: Vejvoda
authors.forename: Ondrej
authors.initials: O
authors.lastname: Sveda
authors.forename: Ondrej
authors.initials: O
authors.lastname: Kaplan
authors.forename: Vera
authors.initials: V
authors.lastname: Prikrylová
authors.forename: Veronika
authors.initials: V
authors.lastname: Elisáková
authors.forename: Michal
authors.initials: M
authors.lastname: Himl
authors.forename: David
authors.initials: D
authors.lastname: Kubác
authors.forename: Helena
authors.initials: H
authors.lastname: Pelantová
authors.forename: Marek
authors.initials: M
authors.lastname: Kuzma
authors.forename: Vladimír
authors.initials: V
authors.lastname: Kren
authors.forename: Ludmila
authors.initials: L
authors.lastname: Martínková
mesh_terms: 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
chemical_list: D000577:Amides; D006571:Heterocyclic Compounds; D009570:Nitriles; D000619:Aminohydrolases; C021867:nitrilase