Application of pig liver esterase catalyzed transesterification in organic media to the kinetic resolution of glycerol derivatives

Tetrahedron Asymmetry

Volumn 10, Issue 19, 1999, Pages 3747-3758

  Jungen, Manfred ^a   Gais, Hans Joachim ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; ESTERASE; GLYCEROL DERIVATIVE; LIVER ENZYME; ORGANIC SOLVENT; PROPIONIC ACID; TOLUENE; VINYL ACETATE; VINYL DERIVATIVE; WATER;

ARTICLE; CATALYSIS; ENANTIOMER; ESTERIFICATION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; PRIORITY JOURNAL; STEREOCHEMISTRY; SWINE;

EID: 0033429257     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00380-8     Document Type: Article

References (66)

1. Ohno, M.; Otsuka, M. Org. React. 1989, 37, 1.
2. Zhu, L.-M.; Tedford, M. C. Tetrahedron 1990, 46, 6587.
3. Gais, H.-J. In Enzyme Catalysis in Organic Synthesis; Drauz, K.; Waldmann, H., Eds.; VCH: Weinheim, 1995; Vol. I, p. 165.
4. Gais, H.-J.; Lukas, K. L. In Preparative Biotransformations; Roberts, S. M.; Wiggins, K.; Casy, G., Eds.; Wiley: New York, 1992-1997; Part 1.
5. Cambou, B.; Klibanov, A. M. J. Am. Chem. Soc. 1984, 106, 2687.
6. Kirchner, G.; Scollar, M. P.; Klibanov, A. M. J. Am. Chem. Soc. 1985, 107, 7072.
7. Heiss, L.; Gais, H.-J. Tetrahedron Lett. 1995, 36, 3833.
8. Ruppert, S.; Gais, H.-J. Tetrahedron: Asymmetry 1997, 8, 3657.
9. Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447.
10. Lemaire, M.; Jeminet, G.; Gourcy, J.-G.; Dauphin, G. Tetrahedron: Asymmetry 1993, 4, 2101.
11. Zhang, D.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1270.
12. Golding, B. T.; Griffin, A. L.; Robinson, D. H. Tetrahedron Lett. 1993, 34, 6459.
13. Ladner, W. E.; Whitesides, G. M. J. Am. Chem. Soc. 1984, 106, 7250.
14. Sonnet, P. E. J. Org. Chem. 1987, 52, 3477.
15. Fuganti, C.; Grasselli, P.; Servi, S.; Lazzarini, A.; Casati, P. J. Chem. Soc., Chem. Commun. 1987, 538.
16. Terao, Y.; Tsuji, K.; Murata, M.; Achiwa, K.; Nishio, T.; Watanabe, N.; Seto, K. Chem. Pharm. Bull. 1989, 37, 1653.
17. Parmar, V. S.; Prasad, A. K.; Singh, P. K.; Gupta, S. Tetrahedron: Asymmetry 1992, 3, 1395.
18. Partali, V.; Melbye, A. G.; Alvik, T.; Anthonsen, T. Tetrahedron: Asymmetry 1992, 3, 65.
19. Waagen, V.; Hollingsaeter, I.; Partali, V.; Thorstad, O.; Anthonsen, T. Tetrahedron: Asymmetry 1993, 4, 2265.
20. Bosetti, A.; Bianchi, D.; Cesti, P.; Golini, P. Biocatalysis 1994, 9, 71.
21. Yi, L; Ward, O. P. J. Ind. Microbiol. 1994, 13, 49.
22. Pallavicini, M.; Valoti, E.; Villa, L.; Piccolo, O. J. Org. Chem. 1994, 59, 1751.
23. Phung, A. N.; Braun, J.; Le Goffic, F. Synth. Commun. 1995, 25, 1783.
24. Hess, R.; Bornscheuer, U.; Capewell, A.; Scheper, T. Enzyme Microbiol. Chem. 1995, 17, 725.
25. Bornscheuer, U.; Yamane, T. J. Am. Oil Chem. Soc. 1995, 72, 193.
26. Bornscheuer, U.; Gaziola, L.; Schmid, R. D. Ann. N.Y. Acad. Sci. 1996, 799, 757.
27. Gaziola, L.; Bornscheuer, U.; Schmid, R. D. Enantiomer 1996, 1, 49.
28. Krebsfänger, N.; Schierholz, K.; Bornscheuer, U. Biotechnol. 1998, 60, 105.
29. Molinari, F.; Brenna, O.; Valenti, M.; Aragozzini, F. Enzyme Microbiol. Technol. 1996, 19, 551.
30. Matsumoto, K.; Fuwa, S.; Shimojo, M.; Kitajima, H. Bull. Chem. Soc. Jpn. 1996, 69, 2977.
31. Vänttinen, E.; Kanerva, L. T. J. Chem. Soc., Perkin Trans. 1 1994, 3459.
32. Vänttinen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1996, 7, 3037.
33. Vänttinen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1997, 8, 923.
34. Janes, L. E.; Löwendahl, A. C.; Kazlauskas, R. J. Chem. Eur. J. 1998, 4, 2324.
35. Takashi, S.; Tetsuo, K.; Yukie, T.; Tadasi, E.; Masanori, U. Tetrahedron Lett. 1998, 39, 7881.
36. For a resolution using alcohol dehydrogenases, see: Geerlof, A.; van Tol, J. B. A.; Jongejan, J. A.; Duine, J. A. Biosci. Biotech. Biochem. 1994, 58, 1028.
37. For the lipase catalyzed enantioselective synthesis of glycerol ethers, see: (a) Breitgoff, D.; Laumen, K.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 1523. (b) Kerscher, V.; Kreiser, W. Tetrahedron Lett. 1987, 28, 531. (c) Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200.
38. For the lipase catalyzed enantioselective synthesis of glycerol ethers, see: (a) Breitgoff, D.; Laumen, K.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 1523. (b) Kerscher, V.; Kreiser, W. Tetrahedron Lett. 1987, 28, 531. (c) Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200.
39. For the lipase catalyzed enantioselective synthesis of glycerol ethers, see: (a) Breitgoff, D.; Laumen, K.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1986, 1523. (b) Kerscher, V.; Kreiser, W. Tetrahedron Lett. 1987, 28, 531. (c) Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200.
40. For the lipase catalyzed resolution of glycerol ethers, see: (a) Herradon, B.; Cueto, S.; Morcuende, Valverde, S. Tetrahedron: Asymmetry 1993, 4, 845. (b) Theil, F.; Weidner, J.; Ballschuh, S.; Kunath, A.; Schick, H. J. Org. Chem. 1994, 59, 388. Theil, F.; Lemke, K.; Ballschuh, S.; Kunath, A.; Schick, H. Tetrahedron: Asymmetry 1995, 6, 1323. (d) Theil, F. Catalysis Today 1994, 22, 517.
41. For the lipase catalyzed resolution of glycerol ethers, see: (a) Herradon, B.; Cueto, S.; Morcuende, Valverde, S. Tetrahedron: Asymmetry 1993, 4, 845. (b) Theil, F.; Weidner, J.; Ballschuh, S.; Kunath, A.; Schick, H. J. Org. Chem. 1994, 59, 388. Theil, F.; Lemke, K.; Ballschuh, S.; Kunath, A.; Schick, H. Tetrahedron: Asymmetry 1995, 6, 1323. (d) Theil, F. Catalysis Today 1994, 22, 517.
42. For the lipase catalyzed resolution of glycerol ethers, see: (a) Herradon, B.; Cueto, S.; Morcuende, Valverde, S. Tetrahedron: Asymmetry 1993, 4, 845. (b) Theil, F.; Weidner, J.; Ballschuh, S.; Kunath, A.; Schick, H. J. Org. Chem. 1994, 59, 388. Theil, F.; Lemke, K.; Ballschuh, S.; Kunath, A.; Schick, H. Tetrahedron: Asymmetry 1995, 6, 1323. (d) Theil, F. Catalysis Today 1994, 22, 517.
43. For the lipase catalyzed resolution of glycerol ethers, see: (a) Herradon, B.; Cueto, S.; Morcuende, Valverde, S. Tetrahedron: Asymmetry 1993, 4, 845. (b) Theil, F.; Weidner, J.; Ballschuh, S.; Kunath, A.; Schick, H. J. Org. Chem. 1994, 59, 388. Theil, F.; Lemke, K.; Ballschuh, S.; Kunath, A.; Schick, H. Tetrahedron: Asymmetry 1995, 6, 1323. Theil, F. Catalysis Today 1994, 22, 517.
44. Boekelheide, V.; Liberman, L.; Figueras, J.; Krespan, C.; Pennington, F. C.; Tarbell, D. S. J. Am. Chem. Soc. 1949, 71, 3303.
45. Blicke, F. F.; Schumann, E. L. J. Am. Chem. Soc. 1952, 74, 2613.
46. Pfaendler, H. R.; Müller, F. X. Synthesis 1992, 350.
47. Henry, P. M. J. Am. Chem. Soc. 1972, 94, 7316.
48. Baer, E.; Fischer, H. O. L. J. Biol. Chem. 1939, 128, 463.
49. Gelas, J. Bull. Soc. Chim. Fr. 1970, 2341.
50. Chen, C. S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695.
51. The E values were calculated according to Ref. 45 by using the equations for irreversible reactions although reversibility of the transesterifications under the conditions employed cannot be rigorously excluded. However, we observed only a minor dependency of the calculated E values on the extent of conversion of the substrate.
52. Note that acylation of the R-alcohol gives the 5-ester due to a change in the priority sequence of the substituents.
53. Laane, C.; Boeren, S.; Hilhorst, R.; Veeger, C. In Biocatalysis in Organic Media; Laane, C.; Tramper, J.; Lilly, M. D., Eds.; Elsevier: Amsterdam, 1987; p. 65.
54. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: Weinheim, 1988.
55. Weber, H. K.; Zuegg, J.; Faber, K.; Pleiss, J. J. Mol. Catal. B: Enzymatic 1997, 3, 131.
56. The transesterification was carried out on a 1 mmol scale, and the alcohol and the ester have not been isolated.
57. Waagen, V.; Hollingsaeter, I.; Huang, M. S. S.; Anthonsen, T. Acta Chem. Scand. 1994, 48, 506.
58. Biggs, J.; Chapman, N. B.; Wray, V. J. Chem. Soc. (B) 1971, 66.
59. Ferraboschi, P.; Grisenti, P.; Manzocchi, A.; Santaniello, E. Tetrahedron 1994, 50, 10539.
60. R (7)=9.3 min).
61. R (7)=9.3 min).
62. R (7)=9.3 min).
63. Following this procedure PLE has been used repeatedly in the batch-wise resolution of rac-1a without a decrease of the E value: Gais, H.-J.; Jadhav, V., unpublished results.
64. However, recently the isolation and purification of a carboxylesterase from Bacillus coagulans has been described, which exhibited a high selectivity (E=55) in the hydrolysis of the caprylate of rac-1a, see: Ref. 29.
65. Hirth, G.; Saroka, H.; Bannwarth, W.; Barner, R. Helv. Chim. Acta 1983, 66, 1210.
66. Toda, F.; Matsuda, S.; Tanaka, K. Tetrahedron: Asymmetry 1991, 2, 983.