Highly enantioselective biohydrolysis of sec-alkyl sulfate esters with inversion of configuration catalysed by Pseudomonas spp.

European Journal of Organic Chemistry

Volumn , Issue 33, 2007, Pages 5527-5530

  Gadler, Petra ^a   Faber, Kurt ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

Biocatalysis; Biohydrolysis; Enantioselectivity; Enzymes; Inversion of configuration

Indexed keywords

EID: 36349005289     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700637     Document Type: Article

References (29)

1. P. Gadler, K. Faber. Trends Biotechnol. 2007, 25, 83-88.
2. S. R. Wallner, M. Pogorevc, H. Trauthwein, K. Faber, Eng. Life Sci. 2004, 4, 512-516.
3. a) K. Faber. Chem. Eur. J. 2001, 7, 5004-5010;
4. b) P. Gadler, S. M. Glueck, W. Kroutil, B. M. Nestl. B. Larissegger-Schnell, B. T. Ueberbacher, S. R. Wallner, K. Faber, Biochem. Soc. Trans. 2006, 34, 296-300.
5. M. A. Kertesz, FEMS Microbiol. Rev. 1999, 24, 135-175.
6. In the majority of biochemical studies, the stereochemical course of the biohydrolysis (inversion vs. retention) cannot be answered, as nonchiral p-nitrophenyl sulfate was used as the substrate.
7. S. R. Hanson, M. D. Best, C.-H. Wong, Angew. Chem. Int. Ed. 2004, 43, 5736-6763.
8. G. Hagelueken, T. M. Adams, L. Wiehlmann, U. Widow, H. Kolmar, B. Tuemmler, D. W. Heinz, W.-D. Schubert, Proc. Natl. Acad. Sci. USA 2006, 103, 7631-7636.
9. I. Boltes, H. Czapinska, A. Kahnert, R. von Buelow, T. Dierks, B. Schmidt, K. von Figura, M. A. Kertesz, I. Uson, Structure 2001, 9, 483-491.
10. J. Mueller, A. Kahnert, T. Pape, G. M. Sheidrick, W. Meyer-Klaucke, T. Dierks, M. A. Kertesz, I. Uson, Biochemistry 2004, 43, 3075-3088.
11. K. S. Dodgson, G. F. White, J. W. Fitzgerald, Sulfatases of Microbial Origin, CRC Press, Boca Raton, 1982, vols. 1 and 2.
12. B. Bartholomew, K. S. Dodgson, G. W. J. Matcham, D. J. Shaw, G. F. White, Biochem. J. 1977, 165, 575-580.
13. D. J. Shaw, K. S. Dodgson, G. F. White, Biochem. J. 1980, 187, 181-196.
14. J. W. Fitzgerald, Biochem. J. 1975, 149, 477-480.
15. G. W. J. Matcham, B. Bartholomew, K. S. Dodgson, J. W. Fitzgerald, W. J. Payne, FEMS Microbiol. Lett. 1977, 1, 197-200.
16. M. Pogorevc, W. Kroutil, S. R. Wallner, K. Faber, Angew. Chem. Int. Ed. 2002, 41, 4052-4054.
17. M. Pogorevc, K. Faber, Appl. Environ. Microbiol. 2003, 69, 2810-2815.
18. a) F. Theil, Tetrahedron 2000, 56, 2905-2919;
19. b) Z.-W. Guo, C. J. Sih, J. Am. Chem. Soc. 1989, 111, 6836-6841;
20. c) R. Amnion, H. Fischgold, Biochem. Z. 1931, 234, 54-61.
21. M. Pogorevc, U. T. Strauss, T. Riermeier, K. Faber, Tetrahedron: Asymmetry 2002, 13, 1443-1447.
22. S. R. Wallner, B. M. Nestl, K. Faber, Org. Lett. 2004, 6, 5009;
23. S. R. Wallner, B. M. Nestl, K. Faber. Org. Biomol. Chem. 2005, 3, 2652.
24. N. J. Palleroni, R. Kunisawa, R. Contopoulou, M. Doudoroff, Int. J. Syst. Bacteriol. 1973, 23, 333-339.
25. For a complete list of inactive strains see the Supporting Information.
26. a) H. Huber, K. O. Stetter, J. Biotechnol. 1998, 64, 39-52;
27. b) C. Bertoldo, C. Dock, G. Antranikian, Eng. Life Sci. 2004, 4, 521-532.
28. [4]
29. M. Pogorevc, K. Faber, Tetrahedron: Asymmetry 2002, 13, 1435-1441.