Enhanced enantioselectivity and remarkable acceleration on the lipase-catalyzed transesterification using novel ionic liquids

Green Chemistry

Volumn 6, Issue 9, 2004, Pages 437-439

  Itoh, Toshiyuki ^a,b,c,d,e   Han, Shihui ^a   Matsushita, Yuichi ^a   Hayase, Shuichi ^a  

^a TOTTORI UNIVERSITY   (Japan)

^b University of Tokyo ^*

^c UNIVERSITY OF TOKYO   (Japan)

^d OKAYAMA UNIVERSITY   (Japan)

^e Veterinary Dentistry and Oral Surgery   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIISOPROPYL ETHER; HEXANE; IMIDAZOLE DERIVATIVE; ION; OXYGEN; PRASEODYMIUM; SODIUM CHLORIDE; SOLVENT; SULFATE; TRIACYLGLYCEROL LIPASE; VINYL ACETATE;

ANALYTIC METHOD; ARTICLE; BURKHOLDERIA CEPACIA; CATALYSIS; ENANTIOSELECTIVITY; ENZYME SUBSTRATE; LIQUID; REACTION ANALYSIS; TRANSESTERIFICATION;

EID: 8144225663     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b405396f     Document Type: Article

References (35)

1. Reviews, see: (a) C.-H. Wong and G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Pergamon, Oxford, 1994; (b) U. T. Bornscheuer and R. J. Kazlauskas, Hydrolases in Organic Synthesis: Regio- And Stereoselective Biotransformations, John Wiley & Sons Inc., UK, 1999.
2. Reviews, see: (a) C.-H. Wong and G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Pergamon, Oxford, 1994; (b) U. T. Bornscheuer and R. J. Kazlauskas, Hydrolases in Organic Synthesis: Regio- And Stereoselective Biotransformations, John Wiley & Sons Inc., UK, 1999.
3. Reviews, see: (a) T. Itoh, Y. Takagi and H. Tsukube, Trends Org. Chem., 1997, 6, 1-22; (b) H. Theil, Tetrahedron, 2000, 56, 2905-2919.
4. Reviews, see: (a) T. Itoh, Y. Takagi and H. Tsukube, Trends Org. Chem., 1997, 6, 1-22; (b) H. Theil, Tetrahedron, 2000, 56, 2905-2919.
5. (a) D. N. Reinhoudt, A. M. Eondebak, W. F. Nijenhuis, W. Verboom, M. Kloosterman and H. E. Schoemaker, J. Chem. Soc., Chem. Commun., 1989, 399-400;
6. (b) D.-J. Uen, J. F. J. Engbersen and D. N. Reinhoudt, J. Mol. Catal. B: Enzym., 2001, 11, 877-882 and references cited therein.
7. (a) T. Itoh, Y. Takagi, T. Murakami, Y. Hiyama and H. Tsukube, J. Org. Chem., 1996, 61, 2158-2163;
8. (b) Y. Takagi, J. Teramoto, H. Kihara, T. Itoh and H. Tsukube, Tetrahedron Lett., 1996, 37, 4991-4992;
9. (c) K. Mitsukura, H. Choraku, T.-D. San and T. Itoh, Bull. Chem. Soc. Jpn., 1999, 72, 1589-1595 and references cited therein.
10. (a) H. Tsukube, A. Betchaku, Y. Hiyama and T. Itoh, J. Chem. Soc., Chem. Commun., 1992, 1751;
11. (b) Y. L. Khmelnitsky, S. H. Welch, D. S. Clark and J. S. Dordick, J. Am. Chem. Soc., 1994, 116, 2647.
12. K. Griebenow, Y. D. Laureano, A. M. Santos, I. M. Clemente, L. Rodríguez, M. W. Vidal and G. Barletta, J. Am. Chem. Soc., 1999, 121, 8157-8163.
13. (a) R. A. Bhaskar, H. Rehman, B. Krishnakumari and J. S. Yadav, Tetrahedron Lett., 1994, 35, 2611-2614;
14. (b) M. Goto, M. Goto, N. Kamiya and F. Nakashio, Biotechnol. Bioeng., 1995, 45, 27-32;
15. (c) T. Maruyama, S. Nagasawa and M. Goto, Biotechnol. Lett., 2002, 24, 1341-1345;
16. (d) Y. Mine, K. Fukunaga, N. Maruoka, K. Nakano and Y. Sugimura, J. Biosci. Bioeng., 2000, 90, 631-636;
17. (e) S. Ueji, M. Nishimura, R. Kudo, R. Matsumi, R. Watanabe, K. Watanabe and Y. Ebara, Chem. Lett., 2001, 912-913;
18. (f) T. Maruyama, S. Nagasawa and M. Goto, Biotechnol. Lett., 2002, 24, 1341-1345;
19. (g) U. Bora, C. J. Saikia, A. Chetia, A. K. Mishra, B. S. D. Kumar and R. C. Boruah, Tetrahedron Lett., 2003, 44, 9099-9102;
20. (h) T. Maruyama, H. Yamamura, T. Kotani, N. Kamiya and M. Goto, Org. Biomol. Chem., 2004, 2, 1239-1244.
21. (a) H. Kitaguchi, I. Itoh and M. Ono, Chem. Lett., 1990, 1203-1204;
22. (b) K. Watanabe, T. Yoshida and S. Ueji, Chem. Commun., 2001, 1260-1261.
23. C.-S. Chen, Y. Fujimoto, G. Girdauskas and C. J. Sih, J. Am. Chem. Soc., 1982, 102, 7294-7298.
24. S. Park and R. J. Kazlauskas, J. Org. Chem., 2001, 66, 8395-8401.
25. (a) K.-W. Kim, B. Song, M.-Y. Choi and M.-J. Kim, Org. Lett., 2001, 3, 1507-1509;
26. (b) M.-J. Kim, M. Y. Choi, J. K. Lee and Y. Ahn, J. Mol. Catal. B: Enzym., 2003, 26, 115-118.
27. (a) T. Itoh, E. Akasaki, K. Kudo and S. Shirakami, Chem. Lett., 2001, 262-263;
28. (b) S. H. Schöfer, N. Kaftzik, P. Wasserscheid and U. Kragl, Chem. Commun., 2001, 425-426.
29. (a) Y. Murakami and A. Hirata, J. Biosci. Bioeng., 1999, 88, 441-443;
30. (b) Y. Mine, K. Fukunaga, M. Yoshimoto, K. Nakano and Y. Sugimura, J. Biosci. Bioeng., 2001, 92, 539-543;
31. (c) M.-J. Kim, Y. II. Chung, Y. K. Choi, H. K. Lee, D. Kim and J. Park, J. Am. Chem. Soc., 2003, 125, 11494-11495.
32. T. Itoh, N. Ouchi, S. Hayase and Y. Nishimura, Chem. Lett., 2003, 32, 654-655.
33. 3) δ 9.48, 13.20, 13.77, 19.23, 22.30, 25.73, 28.98, 29.11, 29.23, 29.31, 31.35, 31.54, 35.06, 48.01, 61.20, 65.78, 69.68, 69.05, 70.19, 71.12, 72.26, 120.17, 122.65, 143.57 ppm.
34. (a) J. Broos, A. J. W. Visser, J. F. J. Engbersen, W. Verboom, A. Hoek and D. N. Reinhoudt, J. Am. Chem. Soc., 1995, 117, 12657-12663;
35. (b) S. Ueiji, T. Taniguchi, T. Okamoto, K. Watanabe, Y. Ebara and H. Ohta, Bull. Chem. Soc. Jpn., 2003, 76, 399-403.