Kinetics and molecular modelling studies on the stereoselective hydrolysis of enantiomeric esters by dipeptide catalysts

Journal of the Chemical Society, Perkin Transactions 2

Volumn , Issue 4, 1991, Pages 543-548

  Ihara, Yasuji ^a   Asakawa, Satoko ^a   Igata, Kayo ^a   Matsumoto, Yoko ^b   Ueoka, Ryuichi ^b  

^a YAMAGUCHI PREFECTURAL UNIVERSITY   (Japan)

^b SOJO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049082240     PISSN: 1472779X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p29910000543     Document Type: Article

References (59)

1. M.L. Bender, Mechanisms of Homogeneous Catalysis from Protons to Proteins, Wiley-Interscience, New York.
2. J.H. Fendler and E.J. Fendler, Catalysis in Micellar and Macromolecular Systems, Academic Press, New York.
3. C.A. Bunton, Application of Biochemical Systems in Organic Chemistry, Part 2eds. J. B. Jones, C. J. Sih, D. Perlman, Wiley, New York.
4. C.A. Bunton, J. Robinson and M.F. Stam, Tetrahedron Lett., 121.
5. J.M. Brown and C.A. Bunton, J. Chem. Soc., Chem. Commun., 969.
6. J.M. Brown, R.L. Elliott, C.G. Riggs, G. Helmchen and G. Nill, Angew. Chem., Int. Ed. Engl., 20, 890.
7. R.A. Moss and W.L. Sunshine, J. Org. Chem., 39, 1083.
8. R.A. Moss, T.J. Lukas and R.C. Nahas, Tetrahedron Lett., 3851.
9. R.A. Moss, R.C. Nahas and T. Lukas, Tetrahedron Lett., 508.
10. J. Koga, M. Shoshi and N. Kuroki, Nippon Kagaku Kaishi, 1179.
11. K. Yamada, H. Shosenji and H. Ihara, Chem. Lett., 491.
12. K. Yamada, H. Shosenji, H. Ihara and Y. Otubo, Tetrahedron Lett., 2529.
13. H. Ihara, S. Ono, H. Shosenji and K. Yamada, J. Org. Chem., 45, 1623.
14. S. Ono, H. Shosenji and K. Yamada, Tetrahedron Lett., 2391.
15. K. Kon-no, M. Tosaka and A. Kitahara, J. Colloid Interface Sci., 79, 581.
16. K. Kon-no, M. Tosaka and A. Kitahara, J. Colloid Interface Sci., 86, 288.
17. Y. Murakami, A. Nakano, A. Yoshimatsu and K. Fukuya, J. Am. Chem. Soc., 103, 728.
18. Y. Murakami, A. Nakano, H. Ikeda, I. Imori and K. Akiyoshi, Bull. Chem. Soc. Jpn., 58, 172.
19. R. Ueoka, T. Terao and K. Ohkubo, Nippon Kagaku Kaishi, 462.
20. K. Ohkubo, K. Sugahara, K. Yoshinaga and R. Ueoka, J. Chem. Soc., Chem. Commun., 393.
21. K. Ohkubo, K. Sugahara, H. Ohta, K. Tokuda and R. Ueoka, Bull. Chem. Soc. Jpn., 54, 576.
22. K. Ohkubo, N. Matsumoto and H. Ohta, J. Chem. Soc., Chem. Commun., 738.
23. R. Ueoka and Y. Murakami, J. Chem. Soc., Perkin Trans. 2, 219.
24. R. Ueoka, Y. Matsumoto, T. Nagamatsu and S. Hirohata, Tetrahedron Lett., 1363.
25. R. Ueoka and Y. Matsumoto, J. Org. Chem., 49, 3774.
26. R. Ueoka, Y. Matsumoto and Y. Ihara, Chem. Lett., 1809.
27. R. Ueoka, R.A. Moss, S. Swarup, Y. Matsumoto, G. Strauss and Y. Murakami, J. Am. Chem. Soc., 107, 2185.
28. R. Ueoka, Y. Matsumoto, N. Takemiya and Y. Ihara, Chem. Pharm. Bull. Jpn., 37, 2263.
29. Y. Ihara, J. Chem. Soc., Chem. Commun., 984.
30. Y. Ihara, J. Chem. Soc., Perkin Trans. 2, 1483.
31. Y. Ihara, M. Nango and N. Kuroki, J. Org. Chem., 45, 5009.
32. Y. Ihara, R. Hosako, M. Nango and N. Kuroki, J. Chem. Soc., Chem. Commun., 393.
33. Y. Ihara, R. Hosako, M. Nango and N. Kuroki, J. Chem. Soc., Perkin Trans. 2, 5.
34. Y. Ihara, N. Kunimasa, T. Kunikiyo, M. Nango and N. Kuroki, Chem. Lett., 667.
35. Y. Ihara, Y. Kimura, M. Nango and N. Kuroki, Makromol. Chem., Rapid Commun., 3, 521.
36. Y. Ihara, Y. Kawamura, E. Nakanishi, M. Nango and J. Koga, Macromol. Chem., Rapid. Commun., 6, 829.
37. Y. Ihara, N. Kunikiyo, T. Kunimasa, Y. Kimura, M. Nango and N. Kuroki, J. Chem. Soc., Perkin Trans. 2, 1741.
38. Y. Ihara, M. Okamoto, Y. Kawamura, E. Nakanishi, M. Nango and J. Koga, J. Chem. Soc., Perkin Trans. 2, 607.
39. Y. Ihara, E. Nakanishi, A. Akiyama and H. Yamamoto, J. Polym. Sci., Polym. Chem. Ed., 27, 87.
40. Y. Ihara, K. Igata, Y. Okubo and M. Nango, J. Chem. Soc., Chem. Commun., 1900.
41. M. Nango, Y. Kimura, Y. Ihara and N. Kuroki, Macromolecules, 21, 2330.
42. R. Ueoka, Y. Matsumoto, T. Yoshino, T. Hirose, J. Kikuchi and Y. Murakami, Chem. Lett., 127.
43. R. Ueoka, Y. Matsumoto, T. Yoshino, N. Watanabe, K. Omura and Y. Murakami, Chem. Lett., 1743.
44. R. Ueoka, Y. Matsumoto, R.A. Moss, S. Swarup, A. Sugii, K. Harada, J. Kikuchi and Y. Murakami, J. Am. Chem. Soc., 110, 1588.
45. F.A. Momany, R.F. McGuire, A.W. Burgess and H.A. Scheraga, J. Phys. Chem., 79, 2361.
46. M. Sisido, personal communication.
47. Y. Beppu, Comput. Chem., 13, 101.
48. M.J.S. Dewar and W. Thiel, J. Am. Chem. Soc., 99, 4899.
49. W. Thiel, J. Am. Chem. Soc., 103, 1413.
50. W. Thiel, J. Am. Chem. Soc., 103, 1420.
51. I. Cho and G. Kim, J. Org. Chem., 53, 5189.
52. K. Ohkubo, M. Kawata, T. Oritto and H. Ishida, J. Chem. Soc., Perkin Trans 1, 666.
53. N. Harada and K. Nakanishi, Circular Dichroic Spectroscopy Excition Coupling in Organic and Bioorganic Chemistry, University Science Books, Mill Valley, CA, USA.
54. G. Halzwarth and P. Doty, J. Am. Chem. Soc., 87, 218.
55. Y.-H. Chen, J.T. Yang and K.H. Chan, Biochemistry, 13, 3350.
56. T. Higashijima, K. Wakamatsu, M. Takimitsu, M. Fujino, T. Nakajima and T. Miyazawa, FEBS Lett., 152, 227.
57. IUPAC-IUB, Biochemistry, 9, 3471.
58. P.N. Lewis, F.A. Momany and H.A. Scheraga, Biochim. Biophys. Acta, 303, 211.
59. S. Miyamoto and M. Yoshimoto, Chem. Pharm. bull., 33, 4856.