Remarkable enhancement of lipase catalytic activity: Combined effects of acyl donor and thiacrown ether additive during trans-esterification of 5-phenyl-1-penten-3-ol

Chemistry Letters

Volumn , Issue 12, 1997, Pages 1247-1248

  Takagi, Yumiko ^a   Ino, Rieko ^a   Kihara, Hiroshi ^a   Itoh, Toshiyuki ^b   Tsukube, Hiroshi ^c  

^a HYOGO UNIVERSITY OF TEACHER EDUCATION   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

^c Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002525289     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.1247     Document Type: Article

References (13)

1. A review see: C. -H. Wong and G. M. Whitesides," Enzymes in Synthetic Organic Chemistry," Pergamon, Oxford (1994).
2. A review see: T. Itoh, Y. Takagi, and H. Tsukube, Trends in Organic Chemistry, 6, 1 (1997). References cited therein.
3. T. Itoh, Y. Takagi, T. Murakami, Y. Hiyama, and H. Tsukube, J. Org. Chem., 61, 2158 (1996); T. Itoh, Y. Takagi, T. Murakami, Y. Hiyama, and H. Tsukube," Preparative Biotransformations," ed by C. Todd, John Wiley & Sons, Chichester, UK(1996), 1:21.1-1:21-5.
4. T. Itoh, Y. Takagi, T. Murakami, Y. Hiyama, and H. Tsukube, J. Org. Chem., 61, 2158 (1996); T. Itoh, Y. Takagi, T. Murakami, Y. Hiyama, and H. Tsukube," Preparative Biotransformations," ed by C. Todd, John Wiley & Sons, Chichester, UK(1996), 1:21.1-1:21-5.
5. Y. Takagi, J. Teramoto, H. Kihara, T. Itoh, and H. Tsukube, Tetrahedron Lett., 37, 4991 (1996).
6. a) T. Miyazawa, S. Kurita, S. Ueji, T. Yamada, and S. Kuwata, J. Chem. Soc. Perkin Trans.1, 1992, 2253.
7. b) T. Ema, S. Maeno, Y. Takaya, T. Sakai, and M. Utaka, Tetrahedron Asymm., 7, 625(1996).
8. Various types of vinyl esters are commercially avairable. To be addressed. Mr. Soji Tanioka, Shin-etsu Chemical Co. Ltd. Asahi-Tokai Building, 2-6-1 Otemachi, Chiyoda-ku, Tokyo 100, Japan. Fax +81-3-3246-5372.
9. C. -S. Chen, Y. Fujimoto, G. Girdauskas, and C. J. Sih, J. Am. Chem. Soc. 102, 7294 (1982).
10. We tested vinyl 2-metylhexanoate, vinyl octylate, vinyl pivalate, vinyl benzoate, and vinyl crotonate as acyl donors. However, none of acylated product was obtained when these vinyl esters were used.
11. a) D. N. Reinhoudt, A. M. Eondebak, W. F. Nijenhuis, W. Verboom, M. Kloosterman, and H. E. Schoemaker, J. Chem. Soc., Chem. Commun., 1989, 399.
12. b) J. F. J. Engbersen, J. Broos, W. Verboom, and D. N. Reinhoudt, Pure & Appl. Chem., 68, 2171(1996).
13. Both the enantioselectivity and relative rate were dropped significantly (E=13, rate=14) when 5 mol% of 18-crown-6 was used as an additive instead of thiacrown ether4 in the reaction of vinyl chloroacetate.