Effects of chemical modification of lipase on its enantioselectivity in organic solvents

Chemistry Letters

Volumn , Issue 10, 2001, Pages 1066-1067

  Ueji, Shin ichi ^a   Tanaka, Hiroyuki ^a   Hanaoka, Takahito ^a   Ueda, Ai ^a   Watanabe, Keiichi ^a   Kaihatsu, Kunihiro ^a   Ebara, Yasuhito ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035653245     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.1066     Document Type: Article

References (25)

1. a) T. Sugai, Current Org. Chem., 3, 373 (1999).
2. b) G. Carrea and S. Riva, Angew. Chem. Int. Ed., 39, 2226 (2000).
3. a) K. Nakamura, Y. Tanabe, T. Kitayama, and A. Ohta, Tetrahedron Lett., 32, 4941 (1991).
4. b) Y. Okahata, Y. Fujimoto, and K. Ijiro, J. Org. Chem., 60, 2244 (1995).
5. c) T. Itoh, K. Mitsukura, W. Kanphai, Y. Takagi, J. Teramoto, H. Kihara, and H. Tsukube, J. Org. Chem., 62, 9165 (1997).
6. d) A. Sánchez, F. Valero, J. Lafuente, and C. Solà, Enzyme Microb. Technol., 27, 157 (2000).
7. e) J.-S. Shin, S. Luque, and A. M. Klibanov, Biotechnol. Bioeng., 69, 577 (2000).
8. f) F. Theil, Tetrahedron, 56, 2905 (2000).
9. g) M. T. Reetz and K.-E. Jaeger, Chem. Eur. J., 6, 407 (2000).
10. a) Q-M. Gu and C. J. Sih, Biocatalysis, 6, 115 (1992).
11. b) D. Bianchi, E. Battistel, A. Bosetti, P. Cesti, and Z. Fekete, Tetrahedron: Asymmetry, 4, 777 (1993).
12. c) P. L. A. Overbeeke, B. C. Koops, H. M. Verheiji, A. J. Slotboom, M. R. Egmond, J. A. Jongejan, and J. J. Heijnen, Biocatal. Biotransform., 18, 59 (2000).
13. a) T. Okamoto and S. Ueji, Chem. Commun., 1999, 939.
14. b) K. Watanabe and S. Ueji, Biotechnol. Lett., 22, 599 (2000).
15. c) K. Watanabe and S. Ueji, J. Chem. Soc., Perkin Trans. 1, 2001, 1386.
16. d) K. Watanabe, T. Yoshida, and S. Ueji, Chem. Commun., 2001, 1260.
17. e) K. Watanabe and S. Ueji, Biocatal. Biotransform., in press.
18. f) S. Ueji, M. Nishimura, R, Kudo, R. Matsumi, K. Watanabe, and Y. Ebara, Chem. Lett., in press.
19. Y. Takahashi, K. Tanaka, M. Murakami, M. Kawanari, Y. Kawasaki, K. Tatsumi, and H. Okai, Biosci. Biotech Biochem., 59, 809 (1995). In a typical procedure, semi-purified lipase (3.6 g) was added to 200 mL of aqueous buffer (pH 10), stirred for 15 min, and then acylating agent (100 equiv) was added. The reaction mixture was shaken at 10 °C for 24 h.
20. a) T. Okuyama and K. Satake, J. Biochem., 47, 454 (1960).
21. b) A. F. S. A. Habeeb, Anal. Biochem., 14, 328 (1966).
22. C.-S. Chen, Y. Fujimoto, G. Girdaukas, and C. J. Sih, J. Am. Chem. Soc., 104, 7294 (1982).
23. C. Laane, S. Boeren, K. Vos, and C. Veeger, Biotechnol. Bioeng., 30, 81 (1994).
24. M. M. Bradford, Anal. Biochem., 72, 248 (1976).
25. 2)-lipase seems to become less rigid by taking into account a more favorable association of a small amount of water in the reaction medium with the lipase in the hydrophobic solvents such as hexane than in isopropyl ether.