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Microbial and Enzymatic Transformation of Nitriles

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Microbial Reagents in Organic Synthesis

Part of the book series: NATO ASI Series ((ASIC,volume 381))

Abstract

Hydrolysis of nitriles to yield amides or carboxylic acids can be performed under mild conditions (room temperature, neutral pH) using crude enzyme preparations or whole viable microbial cells.

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References

  1. Chin, J. and Kim, J.H. (1990) ‘Katalytische Hydrolyse von Acylnitril zu Acrylamid unter milden Bedingungen’, Angew. Chem. 102, 580–582;

    Article  CAS  Google Scholar 

  2. Chin, J. and Kim, J.H. (1990) ‘Katalytische Hydrolyse von Acylnitril zu Acrylamid unter milden Bedingungen’, Int. Ed. Engl. 29, 523–525.

    Article  Google Scholar 

  3. Bennett, M.A. and Yoshida, T. (1973) ‘Homogeneously catalyzed hydration of nitriles to carboxamides’, J. Org. Chem. 95, 3030–3031.

    CAS  Google Scholar 

  4. Cook, M.J., Forbes, E.J. and Khan, G.M. (1966) ‘Solid-phase catalysis of the hydrolysis of nitriles to amides’, J. Chem. Soc, Chem. Commun., 121–122.

    Google Scholar 

  5. Katritzky, A.R., Pilarski, B. and Urogdi, L. (1989) ‘Efficient conversion of nitriles to amides with basic hydrogen peroxide in dimethyl sulfoxide’, Synthesis 949–950.

    Google Scholar 

  6. Jallageas, J.-C, Arnaud, A. and Galzy, P. (1980) ‘Bioconversions of nitriles and their applications’, Adv. Biochem. Eng. 14, 1–32.

    Article  CAS  Google Scholar 

  7. Linton, E.A. and Knowles, C.J. (1986) ‘Utilization of aliphatic amides and nitriles by Nocardia rhodochrous LL 100–21’, J. Gen. Microbiol. 132, 1493–1501.

    CAS  Google Scholar 

  8. Asano, Y., Fujishiro, K., Tani, Y. and Yamada, H. (1982) ‘Aliphatic nitrile hydratase from Arthrobactor sp. J-1 purification and characterization’, Agric. Biol. Chem. 46, 1165–1174.

    Article  CAS  Google Scholar 

  9. Harper, D.B. (1977) ‘Microbial metabolism of aromatic nitriles. Enzymology of C-N cleavage by Norcardia sp. (Rhodochrous group) NCIB 11216’, Biochem. J. 165, 309–319.

    CAS  Google Scholar 

  10. Nagasawa, T., Nanba, H., Ryuno, K., Takeuchi, K. and Yamada, H. (1987) ‘Nitrile hydratase of Pseudomonas chlororaphis B23 purification and characterization’, Eur. J. Chem. 162,691–698.

    CAS  Google Scholar 

  11. Nagasawa, T., Ryuno, K. and Yamada, H. (1986) ‘Nitrile hydratase of Brevibacterium R312 purification and characterization’, Biochem. Biophys. Res. Commun. 139,1305–1312.

    Article  CAS  Google Scholar 

  12. Arnaud, A., Galzy, P. and Jallageas, J.-C. (1977) ‘Etude de l’acétonitrilase d’une souche de Brevibacterium’, Agric. Biol. Chem. 41, 2183–2191.

    Article  CAS  Google Scholar 

  13. Nagasawa, T. and Yamada, H. (1990) ‘Large-scale bioconversion of nitriles into useful amides and acids’, Biocatalysis, D.A. Abramowicz, ed., Van Nostrand Reinhold, New York, p 277–318.

    Google Scholar 

  14. Hjort, CM., Godtfredsen, S.E. and Emborg, C. (1990) ‘Isolation and characterization of a nitrile hydratase from a Rhodococcus sp.’ J. Chem. Tech. Biotechnol. 48, 217–226.

    CAS  Google Scholar 

  15. Nagasawa, T., Mauger, J. and Yamada, H. (1990) ‘A novel nitrilase, arylacetonitrilase, of Alcaligenes faecalis JM3’, Eur. J. Chem. 194, 765–772.

    CAS  Google Scholar 

  16. Tani, Y., Kurihara, M. and Nishise, H. (1989) ‘Characterization of nitrile hydratase and amidase, which are responsible for the conversion of dinitriles to mononitriles from Corynebacterium sp.’, Agric. Biol. Chem. 53, 3151–3158.

    Article  CAS  Google Scholar 

  17. Yamada, H. (1983) PCT Int. Appl. WO 83 01,784, ‘Microbial production of amides from nitriles’; Chem. Abstr.: 99, 86623j.

    Google Scholar 

  18. Vaughan, P.A., Knowles, C.J. and Cheetham, P.S.J. (1989) ‘Conversion of 3-cyanopyridine to nicotinic acid by Norcardia rhodochrous LL100–21’, Enzyme Microb. Technol. 11, 815–823.

    Article  CAS  Google Scholar 

  19. Nagasawa, T., Mathew, CD., Mauger, J. and Yamada, H. (1988) ‘Nitrile hydratase-catalyzed production of nicotinamide from 3-cyanopyridine in Rhodococcus rhodochrous J-1’, Appl. Environ. Microbiol. 54, 1766–1769.

    CAS  Google Scholar 

  20. Brown, D.J. (1984) ‘Comprehensive heterocyclic chemistry’ vol. 3, part 2B, Boulton, A.J. and McKillop, A., eds., Pergamon Press, Oxford, p 81.

    Google Scholar 

  21. Immobilized nitrilase complex SP 409 from Novo Industri A/S, Denmark. The batch used in this study had a nitrile hydratase activity of 391 HPU g−1 (substrate proprionitrile) and an amidase activity of 159 APU g−1 (substrate propionamide).

    Google Scholar 

  22. de Raadt, A., Klempier, N., Faber, K. and Griengl, H. (1992) ‘Chemoselective enzymatic hydrolysis of aliphatic and alicyclic nitriles’, J. Chem. Soc, Perkin Trans. 1, 137–140.

    Article  Google Scholar 

  23. Klempier, N., de Raadt, A., Faber, K. and Griengl, H. (1991) ‘Selective transformation of nitriles into amides and carboxylic acids by an immobilized nitrilase’, Tetrahedron Lett. 32,341–344.

    Article  CAS  Google Scholar 

  24. Vo-Quang, Y., Marais, D., Vo-Quang, L., Le Goffic, F., Thiery, A., Maestracci, M., Arnaud, A. and Galzy, P. (1987) ‘Bacteria in organic synthesis: γ-alkoxy-α-aminoacids from related α-aminonitriles’, Tetrahedron. Lett. 28, 4057–4060.

    Article  CAS  Google Scholar 

  25. Cohen, M.A., Sawden, J. and Turner, N.J. (1990) ‘Selective hydrolysis of nitriles under mild conditions by an enzyme’, Tetrahedron Lett. 31,7223–7226.

    Article  CAS  Google Scholar 

  26. Klempier, N., de Raadt, A., Griengl, H. and Heinisch, G. (1992) ‘Enzymatic hydrolysis of heterocyclic nitriles’, J. Heterocycl. Chem., in press.

    Google Scholar 

  27. Klempier, N., de Raadt, A., Braunegg, G. and Griengl, H., unpublished results.

    Google Scholar 

  28. Godtfredsen, S.E. and Andresen, O. (1984) ‘Enzymatic process’, Eur. Pat. Appl. (prior. 1.10.1984) 178106.

    Google Scholar 

  29. Hönicke-Schmidt, P. and Schneider, M.P. (1990) ‘Enzymatic hydrolysis of nitriles and dinitriles’, J. Chem. Soc, Chem. Commun., 648–650.

    Google Scholar 

  30. Bengis-Garber, C. and Gutman, A.L. (1989) ‘Selective hydrolysis of dinitriles into cyano-carboxylic acids by Rhodococcus rhodochrous N.C.I.B. 11216’, Appl. Microbiol. Biotechnol. 32, 11–16.

    Article  CAS  Google Scholar 

  31. Nishise, H., Kurihara, M. and Tani, Y. (1987) ‘Microbial synthesis of a tranexamic acid intermediate from dinitrile’, Agric. Biol. Chem. 51, 2613–2616.

    Article  CAS  Google Scholar 

  32. Kobayashi, M., Yanaka, N., Nagasawa, T. and Yamada, H. (1990) ‘Monohydrolysis of an aliphatic dinitrile compound by nitrilase from Rhodococcus rhodochrous K22’, Tetrahedron 46, 5587–5590.

    Article  CAS  Google Scholar 

  33. Hechtberger, P. and Faber, K., unpublished results,

    Google Scholar 

  34. Bengis-Garber, C. and Gutman, A.L. (1988) ‘Bacteria in organic synthesis: selective conversion of 1,3-dicyanobenzene into 3-cyanobenzoic acid’, Tetrahedron Lett. 29, 2589–2590.

    Article  CAS  Google Scholar 

  35. Kobayashi, M., Nagasawa, T. and Yamada, H. (1988) ‘Regiospecfic hydrolysis of dinitrile compounds by nitrilase from Rhodococcus rhodochrous J1’, Appl. Microbiol. Biotechnol. 29, 231–233.

    CAS  Google Scholar 

  36. Arnaud, A., Galzy, P. and Jallageas, J.-C. (1980) ‘Production d’acides α-aminés stéréospecifiques par hydrolyse biologique d’ α-aminonitriles racémiques’, Bull. Soc. Chim. Fr. II, 87–90.

    Google Scholar 

  37. Yamamoto, K., Ueno, Y., Otsubo, K., Kawakami, K. and Komatsu K. (1990) ‘Production of (S)-(+)-ibuprofen from a nitrile compound by Acinetobacter sp. strain AK226’, Appl. Environm. Microbiol. 56, 3125–3129.

    CAS  Google Scholar 

  38. Kakeya, H., Sakai, N., Sugai, T. and Ohta, H. (1991) ‘Microbial hydrolysis as a potent method for the preparation of optically active nitriles, amides and carboxylic acids’, Tetrahedron Lett. 32, 1343–1346.

    Article  CAS  Google Scholar 

  39. Yamamoto, K., Otsubo, K. and Oishi, K. (1989) ‘Process for producing optically active a-substituted organic acid and microorganism and enzyme used therefore’, Eur. Pat. Appl. 348901.

    Google Scholar 

  40. Bianchi, D., Bosetti, A., Cesti, P., Franzosi, G. and Spezia, S. (1991) ‘Stereoselective microbial hydrolysis of 2-aryloxypropionitriles’, Biotechnol. Lett. 13, 241–244.

    Article  CAS  Google Scholar 

  41. Kakeya, H., Sakai, N., Sano, A., Yokoyama, M., Sugai, T. and Ohta, H., (1991) ‘Microbial hydrolysis of 3-substituted glutaronitriles’, Chem. Lett. 1823–1824.

    Google Scholar 

  42. Murakami, N. (1990) ‘A method for the production of an optically active 2-substituted carboxylic acid’, Eur. Pat. 356912 (prior. 29.8.1988).

    Google Scholar 

  43. Berger, B., de Raadt, A., Griengl, H., Hayden, W., Hechtberger, P., Klempier, N. and Faber, K. (1992) ‘Useful hydrolytic enzymes: proteases, lipases and nitrilases’, Pure Appl. Chem., in press.

    Google Scholar 

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De Raadt, A., Klempier, N., Faber, K., Griengl, H. (1992). Microbial and Enzymatic Transformation of Nitriles. In: Servi, S. (eds) Microbial Reagents in Organic Synthesis. NATO ASI Series, vol 381. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-2444-7_17

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  • DOI: https://doi.org/10.1007/978-94-011-2444-7_17

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-5078-4

  • Online ISBN: 978-94-011-2444-7

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