Enantioselective acylation of alcohols catalyzed by lipase QL from Alcaligenes sp.: A predictive active site model for lipase QL to identify the faster reacting enantiomer of an alcohol in this acylation

Tetrahedron Asymmetry

Volumn 7, Issue 6, 1996, Pages 1581-1584

  Naemura, Koichiro ^a   Murata, Masaki ^a   Tanaka, Rie ^a   Yano, Masashi ^a   Hirose, Keiji ^a   Tobe, Yoshito ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

TRIACYLGLYCEROL LIPASE;

ACYLATION; ALCALIGENES; ARTICLE; CATALYSIS; ENANTIOMER; ENZYME ACTIVITY; ENZYME MECHANISM; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0029944009     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00186-3     Document Type: Article

References (20)

1. D. H. G. Crout and M. Chrisen, in Modern Synthetic Methods, ed. R. Scheffold, Springer-Verlag, Berlin, 1989, vol. 5, pp. 1-114; H. G. Davies, R. H. Green, D. R. Kelly and S. M. Roberts, Biotransformation in Preparative Organic Chemistry, Academic Press, London, 1990; E. Santaniello, P. Ferraboschi, P. Grisenti and A. Manzocchi, Chem. Rev., 1992, 92, 1071; C. H. Wong and G. W. Whitesides, Enzymes in Synthetic Organic Chemistry, Tetrahedron Organic Chemistry, vol. 12, 1994; and references cited therein.
2. D. H. G. Crout and M. Chrisen, in Modern Synthetic Methods, ed. R. Scheffold, Springer-Verlag, Berlin, 1989, vol. 5, pp. 1-114; H. G. Davies, R. H. Green, D. R. Kelly and S. M. Roberts, Biotransformation in Preparative Organic Chemistry, Academic Press, London, 1990; E. Santaniello, P. Ferraboschi, P. Grisenti and A. Manzocchi, Chem. Rev., 1992, 92, 1071; C. H. Wong and G. W. Whitesides, Enzymes in Synthetic Organic Chemistry, Tetrahedron Organic Chemistry, vol. 12, 1994; and references cited therein.
3. D. H. G. Crout and M. Chrisen, in Modern Synthetic Methods, ed. R. Scheffold, Springer-Verlag, Berlin, 1989, vol. 5, pp. 1-114; H. G. Davies, R. H. Green, D. R. Kelly and S. M. Roberts, Biotransformation in Preparative Organic Chemistry, Academic Press, London, 1990; E. Santaniello, P. Ferraboschi, P. Grisenti and A. Manzocchi, Chem. Rev., 1992, 92, 1071; C. H. Wong and G. W. Whitesides, Enzymes in Synthetic Organic Chemistry, Tetrahedron Organic Chemistry, vol. 12, 1994; and references cited therein.
4. D. H. G. Crout and M. Chrisen, in Modern Synthetic Methods, ed. R. Scheffold, Springer-Verlag, Berlin, 1989, vol. 5, pp. 1-114; H. G. Davies, R. H. Green, D. R. Kelly and S. M. Roberts, Biotransformation in Preparative Organic Chemistry, Academic Press, London, 1990; E. Santaniello, P. Ferraboschi, P. Grisenti and A. Manzocchi, Chem. Rev., 1992, 92, 1071; C. H. Wong and G. W. Whitesides, Enzymes in Synthetic Organic Chemistry, Tetrahedron Organic Chemistry, vol. 12, 1994; and references cited therein.
5. Th. Oberhauser, K. Faber and H. Griehgl, Tetrahedron, 1989, 45, 1682; J. Ehrler and D. Seebach, Liebigs Ann. Chem., 1990, 379; R. J. Kazlauskas, A. M. E. Weissfloch, A. T. Rappaport and L. A. Cuccia, J. Org. Chem., 1991, 56, 2656; C. R. Johnson, A. Golebiowski, T. K. McGill and D. H. Steensma, Tetrahedron Lett., 1991, 32, 2597; K. Burgess and L. D. Jennings, J. Am. Chem. Soc., 1991, 113, 6129; P. G. Hultin and J. B. Jones, Tetrahedron Lett., 1992, 33, 1399; Z. Wimmer, Tetrahedron, 1992, 48, 8431; D. O'Hagan and N. A. Zaidi, J. Chem. Soc., Perkin Trans. 1, 1992, 947; M. J. Kim and Y. K. Choi. J. Org. Chem., 1992, 57, 1605; J. C. Carretero and E. Dominguez, J. Org. Chem., 1992, 57, 3867; M. Tanaka, M. Yoshioka and K. Sakai, Tetrahedron: Asymmetry, 1993, 4, 157.
6. Th. Oberhauser, K. Faber and H. Griehgl, Tetrahedron, 1989, 45, 1682; J. Ehrler and D. Seebach, Liebigs Ann. Chem., 1990, 379; R. J. Kazlauskas, A. M. E. Weissfloch, A. T. Rappaport and L. A. Cuccia, J. Org. Chem., 1991, 56, 2656; C. R. Johnson, A. Golebiowski, T. K. McGill and D. H. Steensma, Tetrahedron Lett., 1991, 32, 2597; K. Burgess and L. D. Jennings, J. Am. Chem. Soc., 1991, 113, 6129; P. G. Hultin and J. B. Jones, Tetrahedron Lett., 1992, 33, 1399; Z. Wimmer, Tetrahedron, 1992, 48, 8431; D. O'Hagan and N. A. Zaidi, J. Chem. Soc., Perkin Trans. 1, 1992, 947; M. J. Kim and Y. K. Choi. J. Org. Chem., 1992, 57, 1605; J. C. Carretero and E. Dominguez, J. Org. Chem., 1992, 57, 3867; M. Tanaka, M. Yoshioka and K. Sakai, Tetrahedron: Asymmetry, 1993, 4, 157.
7. Th. Oberhauser, K. Faber and H. Griehgl, Tetrahedron, 1989, 45, 1682; J. Ehrler and D. Seebach, Liebigs Ann. Chem., 1990, 379; R. J. Kazlauskas, A. M. E. Weissfloch, A. T. Rappaport and L. A. Cuccia, J. Org. Chem., 1991, 56, 2656; C. R. Johnson, A. Golebiowski, T. K. McGill and D. H. Steensma, Tetrahedron Lett., 1991, 32, 2597; K. Burgess and L. D. Jennings, J. Am. Chem. Soc., 1991, 113, 6129; P. G. Hultin and J. B. Jones, Tetrahedron Lett., 1992, 33, 1399; Z. Wimmer, Tetrahedron, 1992, 48, 8431; D. O'Hagan and N. A. Zaidi, J. Chem. Soc., Perkin Trans. 1, 1992, 947; M. J. Kim and Y. K. Choi. J. Org. Chem., 1992, 57, 1605; J. C. Carretero and E. Dominguez, J. Org. Chem., 1992, 57, 3867; M. Tanaka, M. Yoshioka and K. Sakai, Tetrahedron: Asymmetry, 1993, 4, 157.
8. Th. Oberhauser, K. Faber and H. Griehgl, Tetrahedron, 1989, 45, 1682; J. Ehrler and D. Seebach, Liebigs Ann. Chem., 1990, 379; R. J. Kazlauskas, A. M. E. Weissfloch, A. T. Rappaport and L. A. Cuccia, J. Org. Chem., 1991, 56, 2656; C. R. Johnson, A. Golebiowski, T. K. McGill and D. H. Steensma, Tetrahedron Lett., 1991, 32, 2597; K. Burgess and L. D. Jennings, J. Am. Chem. Soc., 1991, 113, 6129; P. G. Hultin and J. B. Jones, Tetrahedron Lett., 1992, 33, 1399; Z. Wimmer, Tetrahedron, 1992, 48, 8431; D. O'Hagan and N. A. Zaidi, J. Chem. Soc., Perkin Trans. 1, 1992, 947; M. J. Kim and Y. K. Choi. J. Org. Chem., 1992, 57, 1605; J. C. Carretero and E. Dominguez, J. Org. Chem., 1992, 57, 3867; M. Tanaka, M. Yoshioka and K. Sakai, Tetrahedron: Asymmetry, 1993, 4, 157.
9. Th. Oberhauser, K. Faber and H. Griehgl, Tetrahedron, 1989, 45, 1682; J. Ehrler and D. Seebach, Liebigs Ann. Chem., 1990, 379; R. J. Kazlauskas, A. M. E. Weissfloch, A. T. Rappaport and L. A. Cuccia, J. Org. Chem., 1991, 56, 2656; C. R. Johnson, A. Golebiowski, T. K. McGill and D. H. Steensma, Tetrahedron Lett., 1991, 32, 2597; K. Burgess and L. D. Jennings, J. Am. Chem. Soc., 1991, 113, 6129; P. G. Hultin and J. B. Jones, Tetrahedron Lett., 1992, 33, 1399; Z. Wimmer, Tetrahedron, 1992, 48, 8431; D. O'Hagan and N. A. Zaidi, J. Chem. Soc., Perkin Trans. 1, 1992, 947; M. J. Kim and Y. K. Choi. J. Org. Chem., 1992, 57, 1605; J. C. Carretero and E. Dominguez, J. Org. Chem., 1992, 57, 3867; M. Tanaka, M. Yoshioka and K. Sakai, Tetrahedron: Asymmetry, 1993, 4, 157.
10. Th. Oberhauser, K. Faber and H. Griehgl, Tetrahedron, 1989, 45, 1682; J. Ehrler and D. Seebach, Liebigs Ann. Chem., 1990, 379; R. J. Kazlauskas, A. M. E. Weissfloch, A. T. Rappaport and L. A. Cuccia, J. Org. Chem., 1991, 56, 2656; C. R. Johnson, A. Golebiowski, T. K. McGill and D. H. Steensma, Tetrahedron Lett., 1991, 32, 2597; K. Burgess and L. D. Jennings, J. Am. Chem. Soc., 1991, 113, 6129; P. G. Hultin and J. B. Jones, Tetrahedron Lett., 1992, 33, 1399; Z. Wimmer, Tetrahedron, 1992, 48, 8431; D. O'Hagan and N. A. Zaidi, J. Chem. Soc., Perkin Trans. 1, 1992, 947; M. J. Kim and Y. K. Choi. J. Org. Chem., 1992, 57, 1605; J. C. Carretero and E. Dominguez, J. Org. Chem., 1992, 57, 3867; M. Tanaka, M. Yoshioka and K. Sakai, Tetrahedron: Asymmetry, 1993, 4, 157.
11. Th. Oberhauser, K. Faber and H. Griehgl, Tetrahedron, 1989, 45, 1682; J. Ehrler and D. Seebach, Liebigs Ann. Chem., 1990, 379; R. J. Kazlauskas, A. M. E. Weissfloch, A. T. Rappaport and L. A. Cuccia, J. Org. Chem., 1991, 56, 2656; C. R. Johnson, A. Golebiowski, T. K. McGill and D. H. Steensma, Tetrahedron Lett., 1991, 32, 2597; K. Burgess and L. D. Jennings, J. Am. Chem. Soc., 1991, 113, 6129; P. G. Hultin and J. B. Jones, Tetrahedron Lett., 1992, 33, 1399; Z. Wimmer, Tetrahedron, 1992, 48, 8431; D. O'Hagan and N. A. Zaidi, J. Chem. Soc., Perkin Trans. 1, 1992, 947; M. J. Kim and Y. K. Choi. J. Org. Chem., 1992, 57, 1605; J. C. Carretero and E. Dominguez, J. Org. Chem., 1992, 57, 3867; M. Tanaka, M. Yoshioka and K. Sakai, Tetrahedron: Asymmetry, 1993, 4, 157.
12. Th. Oberhauser, K. Faber and H. Griehgl, Tetrahedron, 1989, 45, 1682; J. Ehrler and D. Seebach, Liebigs Ann. Chem., 1990, 379; R. J. Kazlauskas, A. M. E. Weissfloch, A. T. Rappaport and L. A. Cuccia, J. Org. Chem., 1991, 56, 2656; C. R. Johnson, A. Golebiowski, T. K. McGill and D. H. Steensma, Tetrahedron Lett., 1991, 32, 2597; K. Burgess and L. D. Jennings, J. Am. Chem. Soc., 1991, 113, 6129; P. G. Hultin and J. B. Jones, Tetrahedron Lett., 1992, 33, 1399; Z. Wimmer, Tetrahedron, 1992, 48, 8431; D. O'Hagan and N. A. Zaidi, J. Chem. Soc., Perkin Trans. 1, 1992, 947; M. J. Kim and Y. K. Choi. J. Org. Chem., 1992, 57, 1605; J. C. Carretero and E. Dominguez, J. Org. Chem., 1992, 57, 3867; M. Tanaka, M. Yoshioka and K. Sakai, Tetrahedron: Asymmetry, 1993, 4, 157.
13. Th. Oberhauser, K. Faber and H. Griehgl, Tetrahedron, 1989, 45, 1682; J. Ehrler and D. Seebach, Liebigs Ann. Chem., 1990, 379; R. J. Kazlauskas, A. M. E. Weissfloch, A. T. Rappaport and L. A. Cuccia, J. Org. Chem., 1991, 56, 2656; C. R. Johnson, A. Golebiowski, T. K. McGill and D. H. Steensma, Tetrahedron Lett., 1991, 32, 2597; K. Burgess and L. D. Jennings, J. Am. Chem. Soc., 1991, 113, 6129; P. G. Hultin and J. B. Jones, Tetrahedron Lett., 1992, 33, 1399; Z. Wimmer, Tetrahedron, 1992, 48, 8431; D. O'Hagan and N. A. Zaidi, J. Chem. Soc., Perkin Trans. 1, 1992, 947; M. J. Kim and Y. K. Choi. J. Org. Chem., 1992, 57, 1605; J. C. Carretero and E. Dominguez, J. Org. Chem., 1992, 57, 3867; M. Tanaka, M. Yoshioka and K. Sakai, Tetrahedron: Asymmetry, 1993, 4, 157.
14. Th. Oberhauser, K. Faber and H. Griehgl, Tetrahedron, 1989, 45, 1682; J. Ehrler and D. Seebach, Liebigs Ann. Chem., 1990, 379; R. J. Kazlauskas, A. M. E. Weissfloch, A. T. Rappaport and L. A. Cuccia, J. Org. Chem., 1991, 56, 2656; C. R. Johnson, A. Golebiowski, T. K. McGill and D. H. Steensma, Tetrahedron Lett., 1991, 32, 2597; K. Burgess and L. D. Jennings, J. Am. Chem. Soc., 1991, 113, 6129; P. G. Hultin and J. B. Jones, Tetrahedron Lett., 1992, 33, 1399; Z. Wimmer, Tetrahedron, 1992, 48, 8431; D. O'Hagan and N. A. Zaidi, J. Chem. Soc., Perkin Trans. 1, 1992, 947; M. J. Kim and Y. K. Choi. J. Org. Chem., 1992, 57, 1605; J. C. Carretero and E. Dominguez, J. Org. Chem., 1992, 57, 3867; M. Tanaka, M. Yoshioka and K. Sakai, Tetrahedron: Asymmetry, 1993, 4, 157.
15. Th. Oberhauser, K. Faber and H. Griehgl, Tetrahedron, 1989, 45, 1682; J. Ehrler and D. Seebach, Liebigs Ann. Chem., 1990, 379; R. J. Kazlauskas, A. M. E. Weissfloch, A. T. Rappaport and L. A. Cuccia, J. Org. Chem., 1991, 56, 2656; C. R. Johnson, A. Golebiowski, T. K. McGill and D. H. Steensma, Tetrahedron Lett., 1991, 32, 2597; K. Burgess and L. D. Jennings, J. Am. Chem. Soc., 1991, 113, 6129; P. G. Hultin and J. B. Jones, Tetrahedron Lett., 1992, 33, 1399; Z. Wimmer, Tetrahedron, 1992, 48, 8431; D. O'Hagan and N. A. Zaidi, J. Chem. Soc., Perkin Trans. 1, 1992, 947; M. J. Kim and Y. K. Choi. J. Org. Chem., 1992, 57, 1605; J. C. Carretero and E. Dominguez, J. Org. Chem., 1992, 57, 3867; M. Tanaka, M. Yoshioka and K. Sakai, Tetrahedron: Asymmetry, 1993, 4, 157.
16. Lipase QL was supplied by Meito Sangyo and used without further purification.
17. C.-S. Chen, Y. Fujimoto, G. Girdaukas and C. Sih, J. Am. Chem. Soc., 1982, 104, 7294.
18. K. Naemura, R. Fukuda, M. Konishi, K. Hirose and Y. Tobe, J. Chem. Soc., Perkin Trans. 1, 1994, 1253; K. Naemura, R. Fukuda, M. Murata, M. Konishi, K. Hirose and Y. Tobe, Tetrahedron Asymmetry, 1995, 6, 2385.
19. K. Naemura, R. Fukuda, M. Konishi, K. Hirose and Y. Tobe, J. Chem. Soc., Perkin Trans, 1, 1994, 1253; K. Naemura, R. Fukuda, M. Murata, M. Konishi, K. Hirose and Y. Tobe, Tetrahedron Asymmetry, 1995, 6, 2385.
20. K. Kato, M. Katayama, R. K. Gautam, S. Fujii and H. Kimoto, Biosci., Biotechnol., Biochem., 1995, 59, 271.