Oxidation of organic cyclic sulfites to sulfates: a new reaction catalyzed by cyclohexanone monooxygenase

Abstract

Cyclohexanone monooxygenase from Acinetobacter catalyzes the enantioselective oxidation of organic cyclic sulfites to sulfates.

References

1. C. T. Walsh and Y. C. J. Chen, Angew. Chem., Int. Ed. Engl., 1988, 27, 333; Angew. Chem., 1988, 100, 342.
2. S. Petit and R. Furstoss, Tetrahedron: Asymmetry, 1993, 4, 1341; R. Gagnon, G. Grogan, M. S. Levitt, S. M. Roberts, P. W. Wan and A. J. Willetts, J. Chem. Soc., Perkin Trans. 1, 1994, 2537.
3. D. R. Light, D. J. Waxman and C. T. Walsh, Biochemistry, 1982, 21, 2490.
4. S. Colonna, N. Gaggero, P. Pasta and G. Ottolina, Chem. Commun., 1996, 2300; G. Carrea, B. Redigolo, S. Riva, S. Colonna, N. Gaggero, E. Battistel and D. Bianchi, Tetrahedron: Asymmetry, 1992, 3, 1063.
5. S. Colonna, N. Gaggero, A. Bertinotti, G. Carrea and P. Pasta, J. Chem. Soc., Chem. Commun., 1995, 1123; S. Colonna, N. Gaggero, G. Carrea, P. Pasta and A. Bernardi, Tetrahedron: Asymmetry, 1996, 7, 565.
6. S. Colonna, N. Gaggero, G. Carrea and P. Pasta, Chem. Commun., 1997, 439.
7. Y. Gao and K. B. Sharpless, J. Am. Chem. Soc., 1988, 110, 7538.
8. H. C. Kolb, M. S. Van Nieuwenhze and K. B. Sharpless, Chem. Rev., 1994, 94, 2483; M. Pilkington and J. D. Wallis, J. Chem. Soc., Chem. Commun., 1993, 1857; B. B. Lohray, Synthesis, 1992, 1035; R. Oi and K. B. Sharpless, Tetrahedron Lett., 1991, 32, 999.
9. H. J. Carlsen and K. Aase, Acta Chem. Scand., 1993, 47, 737.
10. D. G. Hellier and H. G. Liddy, Magn. Reson. Chem., 1988, 26, 671.
11. G. Lowe and M. J. Parrat, Bioorg. Chem., 1988, 16, 283.
12. M. S. Brody and R. Hille, Biochim. Biophys. Acta, 1995, 1253, 133.
13. G. Carrea, P. Pasta, N. Gaggero, G. Grogan and A. J. Willetts, Biotechnol. Lett., 1996, 18, 1123.
14. U. Kragl, W. Kruse, W. Hummel and C. Wandrey, Biotechnol. Bioeng., 1996, 52, 309.
15. S. Rissom, U. Schwarz-Linek, M. Vogel, V. I. Tishkov and U. Kragl, Tetrahedron: Asymmetry, 1997, 8, 2523.
16. J. T. Vincenzi, M. J. Zmjiewski, M. R. Reinhard, B. E. Landen and P. G. Marler, Enzyme Microb. Technol., 1997, 20, 494.
17. J. A. Latham and C. T. Walsh, J. Am. Chem. Soc., 1987, 109, 3421.