Microbial Enantioselective Reduction of Acetylpyridine Derivatives

Bioscience, Biotechnology and Biochemistry

Volumn 67, Issue 4, 2003, Pages 809-814

  Kawano, Shigeru ^a   Horikawa, Miho ^a   Yasohara, Yoshihiko ^a   Hasegawa, Junzo ^a  

^a KANEKA CORPORATION   (Japan)

Author keywords

Acetylpyridine; Candida maris; Enantioselective reduction; Pyridylethanol; Streptomyces

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; GLUCOSE; PYRIDINE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR;

ARTICLE; CANDIDA; HYDROGENATION; METABOLISM; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

ANTI-HIV AGENTS; CANDIDA; GLUCOSE; HYDROGENATION; OXIDATION-REDUCTION; PYRIDINES; REVERSE TRANSCRIPTASE INHIBITORS; STEREOISOMERISM;

CANDIDA; CANDIDA MARIS; HUMAN IMMUNODEFICIENCY VIRUS;

EID: 0042320392     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.67.809     Document Type: Article

References (9)

1. Crosby, J., Chirality in industry-an overview. In “Chirality in Industry”, eds. Collins, A. N., Sheldrake, G. N., and Crosby, J., John Wiley & Sons, Chichester, pp. 1-66 (1995).
2. Wishka, D. G., Graber, D. R., Kopta, L. A., Olmsted, R. A., Friis, J. M., Hosley, J. D., Adams, W. J., Seest, E. P., Castle, T. M., Dolak, L. A., Keiser, B. J., Yagi, Y., Jeganathan, A., Schlachter, S. T., Murphy, M. J., Cleek, G. J., Nugent, R. A., Poppe, S. M., Swaney, S. M., Han, F., Watt, W., White, W. L., Poel, T.-J., Thomas, R. C., Voorman, R. L., Stefanski, K. J., Stehle, R. G., Tarpley, W. G., and Morris, J., (-)-6-Chloro-2-[(1-furo[2,3-c]pyridin-5-ylethyl)thio]-4-pyrimidinamine, PNU-142721, a new broad spectrum HIV-1 non-nucleoside reverse transcriptase inhibitor. J. Med. Chem., 41, 1357-1360 (1998).
3. Wishka, D. G., Grber, D. R., Seest, E. P., Dolak, L. A., Han, F., Watt, W., and Morris, J., Stereoselective synthesis of furo[2,3-c]pyridine pyrimidine thioesters, a new class of potent HIV-1 non-nucleoside reverse transcriptase inhibitors. J. Org. Chem., 63, 7851-7859 (1998).
4. Kula, M.-R., and Kragl, U., Dehydrogenases in the synthesis of chiral compounds. In “Stereoselective Biocatalysis”, ed. Patel, R. N., Marcel Dekker, New York, pp. 839-866 (2000).
5. Matsuda, H., Asamuma, G., Shin, T., Shiono, M., and Kikuyama, S., European Patent Application 911335 (Apr. 28, 1999).
6. Takeshita, M., Terada, K., Akutsu, N., Yoshida, S., and Sato, T., Synthesis of optically active hetero alkylaryl alcohols by baker’s yeast. Heterocycles, 26, 3051-3054 (1987).
7. Bailey, D., O’Hagan, D., Dyer, U., and Lamont, R. B., Preparation of highly enantiopure pyridylethanols by baker’s yeast reduction. Tetrahedron: Asymmetry, 4, 1255-1258 (1993).
8. Bradshaw, C. W., Hummel, W., and Wong, C.-H., Lactobacillus kefir alcohol dehydrogenase: a useful catalyst for synthesis. J. Org. Chem., 57, 1532-1536 (1992).
9. Kizaki, N., Yasohara, Y., Hasegawa, J., Wada, M., Kataoka, M., and Shimizu, S., Synthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate by Escherichia coli transformant cells coexpressing carbonyl reductase and glucose dehydrogenase. Appl. Microbiol. Biotechnol., 55, 590-595 (2001).