A stereoselective inverting sec -alkylsulfatase for the deracemization of sec -alcohols

Organic Letters

Volumn 13, Issue 16, 2011, Pages 4296-4299

  Schober, Markus ^a   Gadler, Petra ^a   Knaus, Tanja ^b   Kayer, Heidemarie ^b   Birner Grünberger, Ruth ^c   Gülly, Christian ^c   MacHeroux, Peter ^b   Wagner, Ulrike ^d   Faber, Kurt ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^c MEDICAL UNIVERSITY OF GRAZ   (Austria)

^d UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKYL SULFATASE; SULFATASE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ENZYME SPECIFICITY; METABOLISM; STEREOISOMERISM;

ALCOHOLS; CATALYSIS; MOLECULAR STRUCTURE; STEREOISOMERISM; SUBSTRATE SPECIFICITY; SULFATASES;

EID: 80051682587     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201635y     Document Type: Article

References (24)

1. Gadler, P.; Faber, K. Trends Biotechnol. 2006, 25, 83-88
2. Kertesz, M. A. FEMS Microbiol. Rev. 2000, 24, 135-175
3. Bojarova, P.; Williams, S. J. Curr. Opin. Chem. Biol. 2008, 12, 573-581
4. Hanson, S. R.; Best, M. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2004, 43, 5736-5763
5. Bornscheuer, U. T.; Kazlauskas, R. J. Hydrolases in Organic Synthesis; Wiley-VCH: Weinheim, 2005.
6. Hagelueken, G.; Adams, T. M.; Wiehlmann, L.; Widow, U.; Kolmar, H.; Tümmler, B.; Heinz, D. W.; Schubert, W.-D. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 7631-7636
7. Boltes, I.; Czapinska, H.; Kahnert, A.; von Bülow, R.; Dierks, T.; Schmidt, B.; von Figura, K.; Kertesz, M. A.; Uson, I. Structure 2001, 9, 483-491
8. Müller, I.; Kahnert, A.; Pape, T.; Sheldrick, G. M.; Meyer-Klaucke, W.; Dierks, T.; Kertesz, M. A.; Uson, I. Biochemistry 2004, 43, 3075-3088
9. Bartholomew, B.; Dodgson, K. S.; Matcham, G. W. J.; Shaw, D. J.; White, G. F. Biochem. J. 1977, 165, 575-580
10. Shaw, D. J.; Dodgson, K. S.; White, G. F. Biochem. J. 1980, 187, 181-196
11. White, G. F. Appl. Microbiol. Biotechnol. 1991, 35, 312-316
12. Fitzgerald, J. W.; Dodgson, K. S.; Matcham, G. W. J. Biochem. J. 1975, 149, 477-480
13. Matcham, G. W. J.; Dodgson, K. S.; Fitzgerald, J. W. Biochem. J. 1977, 167, 723-729
14. Barrett, C. H.; Dodgson, K. S.; White, G. F. Biochem. J. 1980, 191, 467-473
15. Pogorevc, M.; Faber, K. Appl. Environ. Microbiol. 2003, 69, 2810-2815
16. Gadler, P.; Faber, K. Eur. J. Org. Chem. 2007, 5527-5530
17. Angelova, M.; Gadler, P.; Kayer, H.; Krempl, P.; Gülly, C.; Faber, K.; Macheroux, P.; Thallinger, G. Manuscript in preparation.
18. The coordinates of the crystal structure of Pisa1 (2.7 Å resolution) are available from the PDB (code 2YHE); A detailed study on the structural and mechanistic aspects of Pisa1 will be published: Knaus, T.; Schober, M.; Kepplinger, B.; Gadler, P.; Macheroux, P.; Faber, K.; Wagner, U. G. Manuscript in preparation.
19. Batts, B. D. J. Chem. Soc. (B) 1966, 551-555
20. Burwell, R. L., Jr. J. Am. Chem. Soc. 1952, 74, 1462-1466
21. Wallner, S. R.; Nestl, B.; Faber, K. Tetrahedron 2005, 61, 1517-1521
22. Klages, F.; Jung, H. A.; Hegenberg, P. Chem. Ber 1966, 99, 1704-1711
23. Fulford, J. E.; Dupuis, J. W.; March, R. E. Can. J. Chem. 1978, 56, 2324-2330
24. Depending on the conditions, acid-catalyzed sulfate ester hydrolysis may be plagued by racemization, (17) which can be suppressed in the presence of 1,4-dioxane as mediator; see: Batts, B. D. J. Chem. Soc. (B) 1966, 547-551