Regiodivergent Baeyer-Villiger oxidation of fused ketone substrates by recombinant whole-cells expressing two monooxygenases from Brevibacterium

Tetrahedron Letters

Volumn 45, Issue 13, 2004, Pages 2751-2754

  Mihovilovic, Marko D ^a   Kapitán, Peter ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Baeyer Villiger oxidation; Biocatalysis; Biooxidation; Regiodivergent

Indexed keywords

BACTERIAL ENZYME; CARBON; CYCLOBUTANONE DERIVATIVE; KETONE DERIVATIVE; LACTONE DERIVATIVE; UNSPECIFIC MONOOXYGENASE;

ARTICLE; BACTERIAL CELL; BAEYER VILLIGER REACTION; BIOTRANSFORMATION; BREVIBACTERIUM; CARBON NUCLEAR MAGNETIC RESONANCE; ENZYME KINETICS; ESCHERICHIA COLI; GAS CHROMATOGRAPHY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN EXPRESSION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

BREVIBACTERIUM; ESCHERICHIA COLI;

EID: 1542298838     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.036     Document Type: Article

References (30)

1. Mihovilovic M.D., Müller B., Stanetty P. Eur. J. Org. Chem. 2002;3711-3730.
2. Roberts S.M., Wan P.W.H. J. Mol. Catal. B: Enzym. 4:1998;111-136.
3. Walsh C., Chen Y.-C.J. Angew. Chem. 100:1988;342-352.
4. Chen G., Kayser M.M., Mihovilovic M.D., Mrstik M.E., Martinez C.A., Stewart J.D. New J. Chem. 23:1999;827-832.
5. Stewart J.D., Reed K.W., Kayser M.M. J. Chem. Soc., Perkin Trans. 1. 1996;755-757.
6. Mihovilovic M.D., Müller B., Kayser M.M., Stewart J.D., Fröhlich J., Stanetty P., Spreitzer H. J. Mol. Catal. B: Enzym. 11:2001;349-353.
7. Stewart J.D. Curr. Opinion Biotechnol. 11:2000;363-368.
8. Stewart J.D. Biotechnol. Genet. Eng. Rev. 14:1997;67-143.
9. Stewart J.D. Curr. Org. Chem. 2:1998;195.
10. Donoghue N.A., Trudgill P.W. Eur. J. Biochem. 60:1975;1-7.
11. Kyte B.G., Rouviere P., Chen Q., Stewart J.D. J. Org. Chem. 69:2004;12-17.
12. Griffin M., Trudgill P.W. Biochem. J. 129:1972;595-603.
13. Mihovilovic M.D., Müller B., Schultze A., Stanetty P., Kayser M.M. Eur. J. Org. Chem. 2003;2243-2249.
14. Mihovilovic M.D., Müller B., Kayser M.M., Stewart J.D., Stanetty P. Synlett. 2002;703-706.
15. Iwaki H., Hasegawa Y., Wang S., Kayser M.M., Lau P.C.K. Appl. Environ. Microbiol. 68:2002;5671-5684.
16. Mihovilovic M.D., Rudroff F., Müller B., Stanetty P. Bioorg. Med. Chem. Lett. 13:2003;1479-1482.
17. Brzostowicz P.C., Gibson K.L., Thomas S.M., Blasko M.S., Rouviere P.E. J. Bacteriol. 182:2000;4241-4248.
18. Alphand V., Furstoss R. J. Org. Chem. 57:1992;1306-1309.
19. Petit F., Furstoss R. Tetrahedron: Asymmetry. 4:1993;1341-1352.
20. Lebreton J., Alphand V., Furstoss R. Tetrahedron. 53:1997;145-160.
21. Lebreton J., Alphand V., Furstoss R. Tetrahedron Lett. 37:1996;1011-1014.
22. Kelly D.R., Knowles C.J., Mahdi J.G., Taylor I.N., Wright M.A. J. Chem. Soc., Chem. Commun. 1995;729-730.
23. Mehta G., Rao P.S.H. Synth. Commun. 15:1985;991-1000.
24. Ghosez L., Montaigne R., Roussel A., Vanlierde H., Mollet P. Tetrahedron. 27:1971;615-633.
25. Klimko G.P., Davis L.T., Griffin W.B., Sharif A.N. J. Med. Chem. 43:2000;3400-3407.
26. Theil F. Tetrahedron: Asymmetry. 6:1995;1693-1698.
27. Johnson C.R., Nerurkar B.M., Golebiowski A., Sundram H., Esker J.L. J. Chem. Soc., Chem. Commun. 1995;1139-1140.
28. Resul B., Stjernschantz J., No K., Liljebris C., Selén G., Astin M., Karlsson M., Bito Z.L. J. Med. Chem. 36:1993;243-248.
29. Alphand V., Archelas A., Furstoss R. Tetrahedron Lett. 30:1989;3663-3664.
30. Aoki M., Seebach D. Helv. Chim. Acta. 84:2001;187-207.