Synthesis of DL-threo-3-(1-fluoro-1-methylethyl)-and DL-threo-3-(1,1-difluoroethyl)malic acids. mechanistic studies of 3-isopropyl-malate dehydrogenase

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue , 1995, Pages 1905-1912

  Aoyama1, Tetsuya ^a   Eguchi, Tadashi ^a   Oshima, Tairo ^a   Kakinuma, Katsumi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049074286     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19950001905     Document Type: Article

References (25)

1. T. Oshima and K. Imahori, J. Syst. Bacterioi, 1974, 24, 102;
2. T. Tanaka, K. Kawano and T. Oshima, J. Biochem. (Tokyo), 1981, 89, 677;
3. Y. Kagawa, H. Nojima, N. Nukiwa, M. Ishizuka, T. Nakajima, Y. Yasuhara, T. Tanaka and T. Oshima, J. Biol. Chem., 1984, 259, 2956;
4. T. Yamada, N. Akutsu, K. Miyazaki, K. Kakinuma, M. Yoshida and T. Oshima, J. Biochem. (Tokyo), 1990,108, 449.
5. T. Yamada, K. Kakinuma and T. Oshima, Chem. Lett., 1987, 1745.
6. T. Yamada, K. Kakinuma, T. Endo and T. Oshima, Chem. Lett., 1987, 1749.
7. K. Kakinuma, K. Ozawa, Y. Fujimoto, N. Akutsu and T. Oshima, J. Chem. Soc, Chem. Commun., 1989, 1190.
8. T. Nakamoto and B. Vennesland, J. Biol. Chem., 1960, 235, 202;
9. S. England and I. Listowsky, Biochem. Biophys. Res. Commun., 1963,12, 356.
10. K. Imada, M. Sato, N. Tanaka, Y. Katsube, Y. Matsuura and T. Oshima, J. Mol. Biol., 1991, 222, 725.
11. J. H. Hurley and A. M. Dean, Structure, 1994, 2, 1007.
12. H. Terasawa, K. Miyazaki, T. Oshima, T. Eguchi and K. Kakinuma, Biosci. Biotechnol. Biochem., 1994, 58, 870.
13. M. C. Pirrung, H. Han and R. T. Ludwig, J. Org. Chem., 1994, 59, 2423.
14. M. C. Pirrung, H. Han and D. S. Nunn, J. Org. Chem., 1994, 59, 2430.
15. C. T. Walsh, Annu. Rev. Biochem., 1984, 53, 493.
16. C. T. Walsh, Adv. Enzymol. Relat. Areas Mol. Biol, 1983, 55, 197.
17. T. Nakata and T. Oishi, Tetrahedron Lett., 1980, 21, 1641.
18. M. Hudlicky, Org. React., 1988, 35, 513.
19. B. E. Rossiter, T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc, 1981,103,464.
20. T. Eguchi, T. Aoyama and K. Kakinuma, Tetrahedron Lett., 1992, 33, 5545.
21. E. Vedejs, D. A. Emgler and J. E. Telescow, J. Org. Chem., 1978,43, 188.
22. Y. Takenaka, T. Aoyama, T. Eguchi, Y. Ohashi and K. Kakinuma, Anal. Sci., 1994, 10, 519.
23. K. Miyazaki, K. Kakinuma, H. Terasawa and T. Oshima, FEBS Lett., 1993,332,35.
24. H. W. Schnabel, D. Grimm and H. Jensen, Justus Liebigs Ann. Chem., 1974, 477.
25. K. R. Hanson and I. A. Rose, Acc. Chem. Res., 1975, 8, 1.