Lipase PS (Pseudomonas cepacia) mediated resolution of γ-substituted γ-((acetyloxy)methyl)-γ-butyrolactones: Complete stereochemical reversion by substituents

Journal of Organic Chemistry

Volumn 63, Issue 22, 1998, Pages 8062-8066

  Ha, Hyun Joon ^a   Yoon, Kyung Noh ^a   Lee, Sang Youn ^a   Park, Young Soo ^a   Lim, Moon Soo ^a   Yim, Yoon Gil ^a  

^a Hankuk University of Foreign Studies   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000050692     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981184r     Document Type: Article

References (52)

1. (a) Poppe, L.; Novak, L. Selective Biocatalysis; VCH: Wcinheim, Germany, 1992.
2. (b) Haigas, J. Biocatalysis in Organic Synthesis', Elsevier: New York, 1992.
3. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994.
4. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH: Weinheim, Germany, 1995.
5. (e) Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer-Verlag: Heidelberg, Germany, 1997.
6. (f) Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989,28, 695.
7. (g) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071.
8. (h) E. Schoffers; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996,52, 3769.
9. Roberts, S. M.; Williamson, N. M. Curr. Org. Chem. 1997, 1, 1.
10. (a) Russell, S. T.; Robinson, J. A.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1987, 351.
11. (b) Gutman, A. L.; Zuobi, K.; Boltansky, A. Tetrahedron Lett. 1987, 28, 3861.
12. Gutman, A. L.; Bravdo, T. J. Org. Chem. 1989, 54, 4263.
13. Gutman, A. L.; Guibe-Jampel, E. Tetrahedron Lett. 1990,31, 2037.
14. (e) Gutman, A. L.; Zuboi, K.; Bravdo, T. J. Org. Chem. 1990,55,3546.
15. (f) Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415.
16. (g) van der Been, H.; Hof, R. P.; van Oeveren, A.; Feringa, B. L.; Kellogg, R. M. Tetrahedron Lett. 1994, 35,8441.
17. (h) Takahata, IL; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201.
18. Ha, H.-J.; Yi, D.-G.; Yoon, K. N.; Song, C. W. Bull. Kor. Chem. Soc. 1996, 17, 544.
19. (j) van der Deen; Cuiper, A. D.; Hof, R. P.; van Oeveren, A.; Ferigna, B. L.; Kellogg, R. M. J. Am. Chem. Soc. 1996, 118, 3801.
20. Lipase PS is the industrial grade enzyme isolated from the microbe Pseudomonas cepacia that was previously classified as Pseudomonas fluorescens.
21. (a) Kazlauskas, R. J.; Weissfloch, A. N. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656.
22. (b) Xie, Z.-F.; Suemune, H.; Sakai, K. Tetrahedron: Asymmetry 1990, 1, 395.
23. Xie, Z.-F. Tetrahedron: Asymmetry 1991,2, 733.
24. Kirn, M.-J.; Cho, H. J. Chem Soc., Chem. Commun. 1992,1411.
25. (e) Weissfloch, A. N. E.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 6959.
26. (5) Three-dimensional active site model were proposed on the basis of substrate mapping and molecular modeling for substrates
27. (a) Lcmke, K.; Lemke, M.; Theil, F. J. Org. Chem. 1997, 62, 6268.
28. (b) Grabuleda, X.; Jaime, C.; Guerrero, A. Tetrahedron: Asymmetry 1997, 8, 3675.
29. (6) Preparation of cis-β-substituted-γ-(iodomethyl)-γ-butyrolactones
30. (a) Gonzalez, F. B.; Bartlett, P. A. Org. Synth. 1985, 64, 175.
31. (b) Evans, R. D.; Magee, J. W.; Schauble, J. H. Synthesis 1988, 862.
32. 2O (10:1, v/v) under reflux. The ratios offrons and cis were obtained as 91:9, 94:6, and 96:4 for the substrate of β-methyl, ethyl, and phenyl-γ-iodomethyl-γ-butyrolactones, respectively. Details including the medium effect will be reported elsewhere.
33. 3 for the substrates of 1a, 2a, and 4a.
34. (a) Vigneron, J. P.; Meric, R.; Larcheveque, M.; Debal, A.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron Lett. 1982,23,5051.
35. (b) Ortuno, R. M.; Merce, R.; Font, J. Tetrahedron 1987, 43, 4497.
36. (a) Najera, C.; Yus, M.; Seebach, D. Helv. Chim. Acta 1984, 67, 289.
37. (b) Mattes, H.; Hamada, K.; Benezra, C. J. Med. Chem. 1987,30, 1948.
38. (a) Jefiord, C. W.; Sledeski, A. \V.; Boukouvalas, J. Helv. Chim. Acta 1989, 72, 1362.
39. (b) Miyata, O.; Shinada, T.; Kawakami, N.; Taji, K.; Ninomiya, I.; Naito, T.; Data, T.; Okawara, K. Chem. Pharm. Bull. 1992, 40, 2579.
40. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 36, 1017.
41. Herdeis, C.; Lutsch, K.; Waibel, D. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 41.
42. (a) Agarwal, S. K; Rastogi, R. P. Phytochemistry 1978,17,1663.
43. (b) Ortuno, R. M.; Bigorra, J.; Font, J. Tetrahedron 1987,43, 2199.
44. Sato, T.; Okumura, Y.; Itai, J.; Fujisawa, T. Chem. Lett. 1988, 1537.
45. Bocckman, R. K., Jr.; Charctte, A. B.; Asberom, T.; Johnston, B. H. J. Am. Chem. Soc. 1991, 113, 5337.
46. (e) Gibson, C. L.; Handa, S. Tetrahedron: Asymmetry 1996, 7, 1281.
47. Substrates la and 2a,b were hydrolyzed with relatively poor enantiodifferentiation by porcine pancreas lipase in phosphate buffer. We could obtain (+)-lb, (+)-2b, and (+)-3b with 54, 23, and 29% ee's of products at 47,44, and 55% conversion. The absolute configurations of the γ-position for all three favorable substrate lactones are S regardless of substituents at the β-position.
48. (a) Hughes, D. L.; Bergan, J. J.; Amato, J. S.; Bhupathy, M.; Leazer, J. L.; McNamara, J. M.; Sidler, D. R.; Reider, P. J.; Grabowski, E. J. J J. Org. Chem. 1990, 55, 6252.
49. (b) Sonnet, P. E.; Baillargeon, M. W. Lipid 1991,26, 295.
50. Lee, T.; Jones, J. B. J. Am. Chem. Soc. 1997, 119, 10260.
51. The minimum energy conformer generated by PM3 calculation with the program of ChemSD showed rigidity and informational similarity of the γ-lactone ring between irons- and cis-β-methyl-γ-((acetyloxy)methyl)-y-butyrolactones with opposite dihedral angles of γ-acetoxymethyl groups. However the dihedral angle of one substrate could be changed with an energy less than 1.7 kcal/mol.
52. Mitome, H.; Miyaoka, H.; Nakano, M.; Yaraada, Y. Tetrahedron Lett. 1995, 36, 8231.