Molecular recognition by natural macrocycles. Part II. Esterolytic activity and chiral discrimination of amino acid derivatives by the zwitterionic form of (+)-tubocurarine

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 2, 1999, Pages 353-361

  Godoy Alcántar, Carolina ^a   Nelen, Marina I ^b   Eliseev, Alexey V ^b   Yatsimirsky, Anatoly K ^c  

^a CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

^b UNIVERSITY AT BUFFALO   (United States)

^c UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042726631     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a804353a     Document Type: Article

References (53)

1. For reviews: (a) M. L. Bender and M. Komyiama, Cyclodextrin Chemistry, Springer-Verlag, Berlin, 1978; (b) R. Breslow, Adv. Enzymol., 1986, 58, 1; I. Tabushi, Acc. Chem. Res., 1982, 15, 66; H.-J. Schneider, R. Bush, R. Kramer, U. Schneider and I. Theis, ACS Monogr., Nucleophilicity, 1987, 457; (e) Y. Murakami, J. Kikuchi, Y. Hisaeda and O. Hayashida, Chem. Rev., 1996, 96, 721.
2. For reviews: (a) M. L. Bender and M. Komyiama, Cyclodextrin Chemistry, Springer-Verlag, Berlin, 1978; (b) R. Breslow, Adv. Enzymol., 1986, 58, 1; I. Tabushi, Acc. Chem. Res., 1982, 15, 66; H.-J. Schneider, R. Bush, R. Kramer, U. Schneider and I. Theis, ACS Monogr., Nucleophilicity, 1987, 457; (e) Y. Murakami, J. Kikuchi, Y. Hisaeda and O. Hayashida, Chem. Rev., 1996, 96, 721.
3. For reviews: (a) M. L. Bender and M. Komyiama, Cyclodextrin Chemistry, Springer-Verlag, Berlin, 1978; (b) R. Breslow, Adv. Enzymol., 1986, 58, 1; I. Tabushi, Acc. Chem. Res., 1982, 15, 66; H.-J. Schneider, R. Bush, R. Kramer, U. Schneider and I. Theis, ACS Monogr., Nucleophilicity, 1987, 457; (e) Y. Murakami, J. Kikuchi, Y. Hisaeda and O. Hayashida, Chem. Rev., 1996, 96, 721.
4. For reviews: (a) M. L. Bender and M. Komyiama, Cyclodextrin Chemistry, Springer-Verlag, Berlin, 1978; (b) R. Breslow, Adv. Enzymol., 1986, 58, 1; I. Tabushi, Acc. Chem. Res., 1982, 15, 66; H.-J. Schneider, R. Bush, R. Kramer, U. Schneider and I. Theis, ACS Monogr., Nucleophilicity, 1987, 457; (e) Y. Murakami, J. Kikuchi, Y. Hisaeda and O. Hayashida, Chem. Rev., 1996, 96, 721.
5. For reviews: (a) M. L. Bender and M. Komyiama, Cyclodextrin Chemistry, Springer-Verlag, Berlin, 1978; (b) R. Breslow, Adv. Enzymol., 1986, 58, 1; I. Tabushi, Acc. Chem. Res., 1982, 15, 66; H.-J. Schneider, R. Bush, R. Kramer, U. Schneider and I. Theis, ACS Monogr., Nucleophilicity, 1987, 457; (e) Y. Murakami, J. Kikuchi, Y. Hisaeda and O. Hayashida, Chem. Rev., 1996, 96, 721.
6. (a) O. S. Tee, M. Bozzi, J. J. Hoeven and T. A. Gadosy, J. Am. Chem. Soc., 1993, 115, 8990;
7. (b) O. S. Tee, Adv. Phys. Org. Chem., 1994, 29, 1.
8. (a) F. Diederich, G. Shürmann and I. Chao, J. Org. Chem., 1988, 53, 2744;
9. (b) I. Chao and F. Diederich, Recl. Trav. Chim., 1993, 112, 335.
10. N. Pirrincioglu, F. Zaman and A. Williams, J. Chem. Soc., Perkin Trans. 1, 1996, 2561.
11. (a) C. G. Alcántar, A. V. Eliseev and A. K. Yatsimirsky, Bioorg. Med. Chem. Lett., 1995, 5, 2993;
12. (b) C. G. Alcántar, A. V. Eliseev and A. K. Yatsimirsky, J. Mol. Recognit., 1996, 9, 54.
13. R. B. Barlow, Br. J. Pharmacol., 1982, 75, 503.
14. Y. Fraenkel, J. M. Gershoni and G. Navon, Biochemistry, 1994, 33, 644.
15. T. Kitae, T. Nakayama and K. Kano, J. Chem. Soc., Perkin Trans. 2, 1998, 207 and references therein.
16. (a) T. H. Webb and C. S. Wilcox, Chem. Soc. Rev., 1993, 20, 383;
17. (b) H.-J. Schneider, Angew. Chem. Int. Ed. Engl., 1993, 32, 848.
18. Y. Murakami, O. Hayashida and Y. Nagai, J. Am. Chem. Soc., 1994, 116, 2611.
19. K. Araki, K. Inada and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1996, 35, 72.
20. (a) J. Dowden, P. D. Edwars and J. D. Kilburm, Tetrahedron Lett., 1997, 38, 1095;
21. (b) Ch. P. Waymark, J. D. Kilburn and I. Gillies, Tetrahedron Lett., 1995, 36, 3051.
22. S. S. Yoon and W. C. Still, J. Am. Chem. Soc., 1993, 115, 823.
23. (a) M. Philipp and M. L. Bender, Proc. Natl. Acad. Sci. USA, 1971, 68, 478;
24. (b) J. C. Powers and J. W. Harper, in Proteinase Inhibitors, eds. A. J. Barrett and G. Salvesen, Elsevier, New York, 1986, p. 69.
25. K. A. Connors, Binding Constants, Wiley, New York, 1987.
26. E. P. Gibson and J. H. Tumbult, Analyst (London), 1979, 104, 582.
27. Y. Kanaoka, Angew. Chem., Int. Ed. Engl., 1977, 16, 137.
28. (a) C. S. Tsai, Arch. Biochem. Biophys., 1982, 213, 635;
29. (b) J. H. Park, B. P. Meriwerther, P. Clodfelder and L. W. Cunningham, J. Biol. Chem., 1961, 236, 131;
30. (c) R. I. Feldman and H. Weiner, J. Biol. Chem., 1972, 247, 267;
31. (d) R. S. Sidhu and A. H. Blair, J. Biol. Chem., 1975, 250, 7894;
32. (e) G. E. Means and M. L. Bender, Biochemistry, 1975, 14, 4989;
33. (f) M. J. Hardmna, P. Valenznela and M. L. Bender, J. Biol. Chem., 1971, 246, 5907.
34. (a) D. J. Hupe and W. P. Jencks, J. Am. Chem. Soc., 1977, 99, 451;
35. (b) S. Ba-Saif, A. K. Luthra and A. Williams, J. Am. Chem. Soc., 1987, 109, 6362.
36. H. M. Chawla and M. Pathak, Bull. Soc. Chim. Fr., 1991, 232.
37. (a) O. S. Tee and X.-X. Du, J. Org. Chem., 1988, 53, 1837;
38. (b) O. S. Tee and X.-X. Du, J. Am. Chem. Soc., 1992, 114, 620;
39. (c) T. A. Gadosy and O. S. Tee, J. Chem. Soc., Perkin Trans. 2, 1994, 715.
40. (a) B. Capon and B. C. Ghosh, J. Chem. Soc. B, 1966, 472;
41. (b) M. N. Khan, J. Mol. Catal., 1987, 40, 195;
42. (c) A. K. Yatsimirsky, K. Yu, Bezsoudnova and I. K. Sakodinskaya, Bioorg. Med. Chem. Lett., 1993, 3, 635.
43. R. M. Smith and A. E. Martell, Critical Stability Constants, Plenum Press, USA, 1975, vol. 4, p. 25.
44. (a) H.-J. Schneider, Chem. Soc. Rev., 1994, 23, 227;
45. (b) H.-J. Schneider and I. Theis, Angew. Chem., Int. Ed. Engl., 1989, 28, 753.
46. J. C. Ma and D. A. Dougherty, Chem. Rev., 1997, 97, 1303.
47. C. D. Reynolds and R. A. Palmer, Acta Crystallogr., Sect. B, 1976, 32, 1431.
48. (a) F. Bressolle, M. Audran, T. N. Pham and J. J. Vallon, J. Chromatogr. B, 1996, 687, 303;
49. (b) D. W. Armstrong, T. Tang, Sh. Chen, Y. Zhou, C. Bagwill and J.-R. Chen, Anal. Chem., 1994, 66, 1473.
50. (a) S. Fanali, J. Chromatogr., 1996, 735, 77;
51. (b) D. W. Armstrong, K. Rundlett and G. L. Reid III, Anal. Chem., 1994, 66, 1690.
52. L. Fabrizzi and A. Poggi, Chem. Soc. Rev., 1995, 24, 197.
53. J. Polster and H. Lachman, Spectrophotometric Titrations, VCH Publishers, Weinheim, 1989.