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Biotransformation of heterocyclic dinitriles by Rhodococcus erythropolis and fungal nitrilases

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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.

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Acknowledgement

Financial support through projects IAA500200708 (Grant Agency of the Academy of Sciences of the Czech Republic), LC06010 and OC D25.001 (Ministry of Education, Czech Republic) and the institutional research concept AV0Z50200510 (Institute of Microbiology) is gratefully acknowledged. We also wish to thank Mrs. Jana Horová for her excellent technical assistance.

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Authors and Affiliations

  1. Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeská 1083, CZ-142 20, Prague 4, Czech Republic

    Vojtěch Vejvoda, Ondřej Šveda, Ondřej Kaplan, Věra Přikrylová, Veronika Elišáková, Michal Himl, David Kubáč, Helena Pelantová, Marek Kuzma, Vladimír Křen & Ludmila Martínková

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  1. Vojtěch Vejvoda
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  2. Ondřej Šveda
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  3. Ondřej Kaplan
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  4. Věra Přikrylová
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  5. Veronika Elišáková
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  6. Michal Himl
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  7. David Kubáč
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  10. Vladimír Křen
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  11. Ludmila Martínková
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Corresponding author

Correspondence to Ludmila Martínková.

Appendix

Appendix

6-Cyanopyridine-2-carboxamide (1b) 1H NMR (399.87 MHz, DMSO-d 6 , 30°C): 7.830 (1 H, br s, NH2-u), 8.211 (1H, dd, J = 7.6, 2.2 Hz, H-5), 8.22 (1H, br s, NH2-d), 8.238 (1 H, dd, J = 7.6, 7.0 Hz, H-4), 8.294 (1H, dd, J = 7.0, 2.2 Hz, H-3). 13C NMR (100.55 MHz, DMSO-d 6 , 30°C): 117.09 (6-CN), 125.88 (C-3), 131.31 (C-5), 131.46 (C-6), 139.75 (C-4), 151.91 (C-2), 164.49 (2-CO).

6-Cyanopyridine-2-carboxylic acid (1e) 1H NMR (399.87 MHz, DMSO-d 6 , 30°C): 8.231 (2 H, m, H-4, H-5), 8.296 (1 H, m, H-3). 13C NMR (100.55 MHz, DMSO-d 6 , 30°C): 117.01 (6-CN), 128.21 (C-3), 131.64 (C-5), 132.57 (C-6), 139.63 (C-4), 150.23 (C-2), 164.77 (2-CO).

2-Cyanopyridine-4-carboxamide (2b) 1H NMR (399.87 MHz, DMSO-d 6 , 30°C): 7.948 (1 H, br s, NH), 8.078 (1 H, dd, J = 5.1, 1.7 Hz, H-5), 8.347 (1 H, dd, J = 1.7, 0.9 Hz, H-3), 8.370 (1 H, br s, NH), 8.904 (1 H, dd, J = 5.1, 0.9 Hz, H-6). 13C NMR (100.55 MHz, DMSO-d 6 , 30°C): 117.29 (2-CN), 125.49 (C-5), 126.69 (C-3), 133.26 (C-2), 142.92 (C-4), 152.11 (C-6), 164.55 (4-CO).

2-Cyanopyridine-4-carboxylic acid (2c) 1H NMR (399.87 MHz, DMSO-d 6 , 30°C): 8.079 (1 H, dd, J = 4.9, 1.3 Hz, H-5), 8.296 (1 H, s, H-3), 8.872 (1 H, d, J = 4.9 Hz, H-6). 13C NMR (100.55 MHz, DMSO-d 6 , 30°C): 117.37 (2-CN), 126.85 (C-5), 128.05 (C-3), 133.25 (C-2), 143.11 (C-4), 152.07 (C-6), 164.82 (4-CO).

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Vejvoda, V., Šveda, O., Kaplan, O. et al. Biotransformation of heterocyclic dinitriles by Rhodococcus erythropolis and fungal nitrilases. Biotechnol Lett 29, 1119–1124 (2007). https://doi.org/10.1007/s10529-007-9364-z

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  • DOI: https://doi.org/10.1007/s10529-007-9364-z

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