Light-mediated regulation of asymmetric reduction of ketones by a cyanobacterium

Tetrahedron Asymmetry

Volumn 13, Issue 23, 2002, Pages 2529-2533

  Nakamura, Kaoru ^a   Yamanaka, Rio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE; ALPHA,ALPHA DIFLUOROACETOPHENONE; DIURON; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYANOBACTERIUM; ENANTIOSELECTIVITY; FLUORESCENT LIGHTING; ILLUMINATION; NONHUMAN; PHOTOSYNTHESIS; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY;

EID: 0037180583     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00683-3     Document Type: Article

References (34)

1. Itoh T., Sakabe K., Kudo K., Ohara H., Takagi Y., Kihara H., Zagatti P., Renou M. J. Org. Chem. 64:1999;252-265.
2. O'Hagan D., Rzepa H.S. J. Chem. Soc., Chem. Commun. 1997;645-652.
3. Ge P., Kirk K.L. J. Org. Chem. 62:1997;3340-3343.
4. Altenburger J.M., Schirlin D. Tetrahedron Lett. 32:1991;7255-7258.
5. Matsuda F., Matsumoto T., Ohsaka M., Terashima S. Tetrahedron Lett. 30:1989;4259-4262.
6. Welch J.T. Tetrahedron. 43:1987;3123-3197.
7. Nakamura K., Matsuda T. Drauz K., Waldmann H. 2nd ed. Enzyme Catalysis in Organic Synthesis. III:2002;991-1047 Wiley-VCH, Weinheim.
8. Fessner W.D. Biocatalysis from discovery to application. 2000;Springer-Verlag, Berlin.
9. Faber K. Biotransformations. 2000;Springer-Verlag, Berlin.
10. Roberts S.M. J. Chem. Soc., Perkin Trans. 1. 2000;611-633.
11. Roberts S.M. J. Chem. Soc., Perkin. Trans. 1. 1999;1-21.
12. Nakamura K., Kawai Y., Nakajima N., Ohno A. J. Org. Chem. 56:1991;4778-4783.
13. Nakamura K., Inoue Y., Matsuda T., Misawa I. J. Chem. Soc., Perkin 1. 1999;2397-2402.
14. Rotthaus O., Krüger D., Demuth M., Schaffner K. Tetrahedron. 53:1997;935-938.
15. Nakamura K., Kondo S., Nakajima N., Ohno A. Tetrahedron. 51:1995;687-694.
16. Nakamura K., Inoue Y., Ohno A. Tetrahedron Lett. 36:1995;265-266.
17. Nakamura K., Fujii M., Ida Y. J. Chem. Soc., Perkin 1. 2000;3205-3211.
18. D'Arrigo P., Fuganti C., Pedrocchi G., Fantoni P., Servi S. Tetrahedron. 54:1998;15017-15026.
19. D'Arrigo P., Lattanzio M., Pedrocchi G., Fantoni P., Servi S. Tetrahedron: Asymmetry. 9:1998;4021-4026.
20. Matsuda T., Nakajima Y., Harada T., Nakamura K. Tetrahedron: Asymmetry. 13:2002;971-974.
21. Matsuda T., Harada T., Nakajima N., Nakamura K. Tetrahedron Lett. 41:2000;4135-4138.
22. Nakamura K., Matsuda T. J. Org. Chem. 63:1998;8957-8964.
23. Scheibe R. Bot. Acta. 103:1990;327-334.
24. Erlanger B.F. Annu. Rev. Biochem. 45:1976;257-283.
25. The yields and the enantioselectivities roughly increased according to light intensities.
26. Nakamura K., Yamanaka R. J. Chem. Soc., Chem. Commun. 2002;1782-1783.
27. Trebst A. Methods Enzymol. 69:1980;675-715.
28. Oxidation of the reduced form of coenzymes by cell free extract of the microbe in the presence of 1 reveal that NADPH is effective but NADH is less effective.
29. Previously, we reported that methyl aryl ketones were reduced to the corresponding (S)-alcohol by S. elongatus PCC 7942 in the light: Nakamura K., Yamanaka R., Tohi K., Hamada H. Tetrahedron Lett. 41:2000;6799-6802.
30. Matsuda T., Harada T., Nakajima N., Itoh T., Nakamura K. J. Org. Chem. 65:2000;157-163.
31. Smith H. Nature. 407:2000;585-591.
32. Ocheretina O., Haferkamp I., Tellioglu H., Scheibe R. Gene. 258:2000;147-154.
33. Gietl C. Biochim. Biophys. Acta. 1100:1992;217-234.
34. Rippka R. Methods Enzymol. 167:1988;675-715.