Rationalisation of the regioselective hydrolysis of aliphatic dinitriles with Rhodococcus rhodochrous AJ270

Abstract

Aliphatic dinitriles undergo regioselective hydrolysis with the title organism to give monoacids with up to four methylenes between the nitrile functions (optimally 2–3) or when either an oxygen is placed β, γ or δ to the nitrile (δ-placement being optimal) or β or γ (optimally γ) but not δ sulfur substituents are present; nitrogen substituents appear to behave as for oxygen but suffer a steric limitation of the size of the nitrogen substituent.

References

1. O. Meth-Cohn and M.-X. Wang, Tetrahedron Lett., 1995, 36, 9561; J. Chem. Soc., Perkin 1, in the press.
2. Y. Asano, S. Ando, Y. Tani and H. Yamada, Agric. Biol. Chem., 1980, 44, 2497; H. Yamada, Y. Asano and Y. Tani, J. Ferment. Technol., 1980, 58, 495.
3. H. Yamada, Y. Asano, Y. Tani, Y. Asano, S. Ando, Y. Tani, H. Yamada and T. Ueno, Agric. Biol. Chem., 1981, 45, 57.
4. C. Bengis-Garber and A. L. Gutman, Tetrahedron Lett., 1988, 29, 2589; Appl. Microbiol. Biotechnol., 1989, 32, 11.
5. M. Kobayashi, N. Yanaka, T. Nagasawa and H. Yamada, Tetrahedron, 1990, 46, 5587.
6. P. Hönicke-Schmidt and M. P. Schneider, J. Chem. Soc., Chem. Commun., 1990, 648.
7. M. A. Cohen, J. Sawden and N. J. Turner, Tetrahedron Lett., 1990, 31, 7223.
8. H. Kakaye, N. Sakai, A. Sano, M. Yokoyama, T. Sugai and H. Ohta, Chem. Lett., 1991, 1823.
9. J. A. Crosby, J. S. Parratt and N. J. Turner, Tetrahedron: Asymmetry, 1992, 3, 1547; A. Kerridge, J. S. Parratt, S. M. Roberts, F. Theil, N. J. Turner and A. J. Willetts, Bioorg. Med. Chem. Lett., 1994, 2, 447; S. Maddrell, N. J. Turner, A. Kerridge, A. J. Willetts and J. A. Crosby, Tetrahedron Lett., 1996, 37, 6001.
10. M. Yokoyama, T. Sugai and H. Ohta, Tetrahedron: Asymmetry, 1993, 4, 1081.
11. H. Nishise, M. Kurihara and Y. Tani, Agric. Biol. Chem., 1987, 51, 2613; Y. Tani, M. Kurihara, H. Nishise and K. Yamamoto, Agric. Biol. Chem., 1989, 53, 3143; Y. Tani, M. Kurihara and H. Nishise, Agric. Biol. Chem., 1989, 53, 3151; K. Yamamoto, Y. Ueno, K. Otsubo, H. Yamane, K.-I. Komatsu and Y. Tani, J. Ferment. Bioeng., 1992, 73, 125.
12. J. L. Moreau, F. Bigey, S. Azza, A. Arnaud and P. Galzy, Biocatalysis, 1994, 10, 325 and references cited therein.
13. T. Nagasawa, H. Namba, K. Ryuno, K. Takeuchi and H. Yamada, Eur. J. Biochem., 1987, 162, 691.
14. J. Crosby, J. Moilliet, J. S. Parratt and N. J. Turner, J. Chem. Soc., Perkin Trans. 1, 1994, 1679 and references cited therein L. Martínková, P. Olšovský, I. Prepechalová and V. Kren, Biotechnol. Lett., 1995, 7, 1219.