Mechanisms for chiral recognition by cyclodextrins

Journal of Physical Organic Chemistry

Volumn 10, Issue 5, 1997, Pages 286-291

  Kano, Koji ^a  

^a DOSHISHA UNIVERSITY   (Japan)

Author keywords

Chiral recognition; Cyclodextrins

Indexed keywords

EID: 0002496179     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1395(199705)10:5<286::AID-POC915>3.0.CO;2-Y     Document Type: Review

References (59)

1. F. Cramer and W. Dietsche, Chem. Ber. 92, 378-385 (1959).
2. K. Kano, in Bioorganic Chemistry Frontiers, edited by H. Dugas and F. P. Schmitchen, Vol. 3, pp. 1-23. Springer, Berlin (1993)
3. E.g. (a) L. H. Easson and E. Stedman, Biochem. J. 27, 1257-1266 (1933); (b) C. E. Dalgliesh, J. Chem. Soc. 3, 3940-3942 (1952); (c) W. H. Pirkle and T. C. Pochapsky, Chem. Rev. 89, 347-362 (1989).
4. E.g. (a) L. H. Easson and E. Stedman, Biochem. J. 27, 1257-1266 (1933); (b) C. E. Dalgliesh, J. Chem. Soc. 3, 3940-3942 (1952); (c) W. H. Pirkle and T. C. Pochapsky, Chem. Rev. 89, 347-362 (1989).
5. E.g. (a) L. H. Easson and E. Stedman, Biochem. J. 27, 1257-1266 (1933); (b) C. E. Dalgliesh, J. Chem. Soc. 3, 3940-3942 (1952); (c) W. H. Pirkle and T. C. Pochapsky, Chem. Rev. 89, 347-362 (1989).
6. R. S. Shallenberger, T. E. Acree and C. Y. Lee, Nature (London) 221, 555-556 (1969).
7. A. G. Ogston, Nature (London) 162, 963 (1948).
8. F. Cramer, in The Lock and Key Principle, edited by J.-P. Behr, pp. 1-23. Wiley, Chichester (1994).
9. H.-J. Schneider, T. Blatter and U. Cuber, in Frontiers in Supramolecular Organic Chemistry and Photochemistry, edited by H.-J. Schneider and H. Dürr, pp. 29-56. VCH, Weinheim (1991).)
10. (a) V. Schurig and H.-P. Notwotny, Angew. Chem., Int. Ed. Engl. 29, 939-957 (1990);
11. (b) S. Li and W. C. Purdy, Chem. Rev. 92, 1457-1470 (1992);
12. (c) S. F. Y. Li, J. Chromatogr. Libr. 52, 201-289 (1992).)
13. (a) K. Kano, K. Matsumoto, S. Hashimoto, M. Sisido and Y. Imanishi, J. Am. Chem. Soc. 107, 6117-6118 (1985);
14. (b) K. Kano, H. Matsumoto, Y. Yoshiyasu and S. Hashimoto, J. Am. Chem. Soc. 110, 204-209 (1988).
15. M. Sisido, Jasco Rep. 34, 1-6 (1992).
16. G. LeBas, C. de Rango, N. Rysanek and G. Tsoucaris, J. Inclus. Phenom. 2, 861-867 (1984).
17. K. Yannakopoulou, D. Mentzafos, I. M. Mavridis and K. Dandika, Angew. Chem. Int. Ed. Engl. 35, 2480-2482 (1996).
18. D. R. Black, C. G. Parker, S. S. Zimmerman and M. L. Lee, J. Comput. Chem. 17, 931-939 (1996).
19. E.g. (a) M. Mikolajczyk and J. Drabowicz, J. Am. Chem. Soc. 100, 2510-2515 (1978); (b) R. Fornasier, F. Reniero, P. Scrimin and U. Tonellato, J. Org. Chem. 50, 3209-3211 (1985); (c) M. Komiyama, J. Am. Chem. Soc. 111, 3046-3050 (1989).
20. E.g. (a) M. Mikolajczyk and J. Drabowicz, J. Am. Chem. Soc. 100, 2510-2515 (1978); (b) R. Fornasier, F. Reniero, P. Scrimin and U. Tonellato, J. Org. Chem. 50, 3209-3211 (1985); (c) M. Komiyama, J. Am. Chem. Soc. 111, 3046-3050 (1989).
21. E.g. (a) M. Mikolajczyk and J. Drabowicz, J. Am. Chem. Soc. 100, 2510-2515 (1978); (b) R. Fornasier, F. Reniero, P. Scrimin and U. Tonellato, J. Org. Chem. 50, 3209-3211 (1985); (c) M. Komiyama, J. Am. Chem. Soc. 111, 3046-3050 (1989).
22. D. A. Lightner, J. K. Gawronski and K. Gawronska, J. Am. Chem. Soc. 107, 2456-2461 (1985).
23. K. Kano, K. Yoshiyasu, H. Yasuoka, S. Hata and S. Hashimoto, J. Chem. Soc., Perkin Trans. 2 1265-1269 (1992).
24. N. Harata and K. Nakanishi, Circular Dichroism Spectroscopy. Exciton Coupling in Organic Stereochemistry. University Science Books, Mill Valley, CA (1983).
25. K. Kano, K. Yoshiyasu and S. Hashimoto, J. Chem. Soc., Chem. Commun. 801-802 (1988).
26. K. Kano, K. Yoshiyasu and S. Hashimoto, Chem. Lett. 21-24 (1990).
27. K. Kano, N. Tsujino and M. Kim, J. Chem. Soc., Perkin Trans. 2 1747-1752 (1992).
28. K. Kano and T. Ishimura, J. Chem. Soc., Perkin Trans. 2 1655-1660 (1995).
29. R. I. Gelb, L. M. Schwartz, J. J. Bradshaw and D. A. Laufer, Bioorg. Chem. 9, 299-304 (1980).
30. M. Komiyama, J. Am. Chem. Soc. 111, 3046-3050 (1989).
31. A. F. Danil de Namor, R. Traboulssi and D. F. V. Lewis, J. Am. Chem. Soc. 112, 8442-8447 (1990).
32. K. B. Lipkowitz, S. Raghothama and J.-a. Yang, J. Am. Chem. Soc. 114, 1554-1562 (1992).
33. G. A. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures Springer, Berlin (1991).
34. (a) H.-J. Schneider, T. Blatter, R. Kramer, S. Kumar, U. Schneider and I. Theis, in Inclusion Phenomena and Molecular Recognition, edited by J. L. Atwood, pp. 65-74. Plenum Press, New York (1990);
35. (b) H.-J. Schneider, T. Schiestel and P. Zimmermann, J. Am. Chem. Soc. 114, 7698-7703 (1992);
36. (c) H.-J. Schneider, T. Blatter, B. Palm, U. Pfingstag, V. Rüdinger and I. Theis, J. Am. Chem. Soc. 114, 7704-7708 (1992);
37. (d) A. V. Eliseev and H.-J. Schneider, Angew. Chem., Int. Ed. Engl. 32, 1331-1333 (1993);
38. (e) A. V. Eliseeve and H.-J. Schneider, J. Am. Chem. Soc. 116, 6081-6088 (1994);
39. (f) W. Tagaki, K. Yano, K. Yamanaka, H. Yamamoto and T. Miyasaka, Tetrahedron Lett. 31, 3897-3900 (1990);
40. (g) W. Tagaki and H. Yamamoto, Tetrahedron Lett. 32, 1207-1208 (1991);
41. (h) A. Echavarren, A. Galan, J.-M. Lehn and J. de Mendoza, J. Am. Chem. Soc. 111, 4994-4995 (1989);
42. (i) A. K. Yatsimirsky and A. V. Eliseev, J. Chem. Soc., Perkin Trans. 2 1769-1772 (1991);
43. (j) R. C. Petter, J. S. Salek, C. T. Sikorski, G. Kumaravel and F.-T. Lin, J. Am. Chem. Soc. 112, 3860-3868 (1990);
44. (k) C. S. Wilcox, E. Kim, D. Romano, L. H. Kuo, A. L. Burt and D. P. Curran, Tetrahedron 51, 621-634 (1995).
45. I. Tabushi, Y. Kuroda and T. Mizutani, J. Am. Chem. Soc. 108, 4514-4518 (1986).
46. A. Cooper and D. D. MacNicol, J. Chem. Soc., Perkin Trans. 2 760-763 (1978).
47. S. E. Brown, J. H. Coates, P. A. Duckworth, S. F. Lincoln, C. J. Easton and B. L. May, J. Chem. Soc., Faraday Trans. 89, 1035-1040 (1993).
48. T. Kitae and K. Kano, in Abstracts of 11th Symposium on Biofunctional Chemistry, Fukuoka, Japan, October 1996.
49. K. Kano, S. Arimoto and T. Ishimura, J. Chem. Soc., Perkin Trans. 2 1661-1666 (1995).
50. R. Corradini, A. Dossena, G. Impellizzeri, G. Maccarrone, R. Marchelli, E. Rizzarelli, G. Sartor and G. Vecchio, J. Am. Chem. Soc. 116, 10267-10274 (1994).
51. S. E. Brown, C. A. Haskard, C. J. Easton and S. F. Lincoln, J. Chem. Soc., Faraday Trans., 91, 1013-1018 (1995).
52. (a) M. Kitagawa, H. Hoshi, M. Sakurai, Y. Inoue and R. Chûjô, Bull. Chem. Soc. Jpn. 61, 4225-4229 (1988);
53. (b) K. Kano, K. Mori, B. Uno, M. Goto and T. Kubota, J. Am. Chem. Soc. 112, 8645-8649 (1990);
54. (c) M. J. Sherrod, in Spectroscopic and Computational Studies of Supramolecular Systems, edited by J. E. D. Davies, pp. 187-205. Kluwer, Dordrecht (1992).
55. K. Kano, K. Yoshiyasu and S. Hashimoto, J. Chem. Soc., Chem. Commun. 1278-1279 (1989).
56. K. Kano, Y. Tamiya, C. Otsuki, T. Shimomura, T. Ohno, O. Hayashida and Y. Murakami, Supramol. Chem. 2, 137-143 (1993).
57. K. Kano, Y. Kato and M. Kodera, J. Chem. Soc., Perkin Trans. 2 1211-1217 (1996).
58. K. Kano, N. Tanaka, H. Minamizono and Y. Kawakita, Chem. Lett. 925-926 (1996).
59. K. Kano, S. Negi, H. Takashima, H. Kamo, R. Takaoka, M. Yamaguchi, H. Okubo and M. Hirama, in Abstracts of Joint Symposia 'Supramolecules and Nano-Organized Systems.' Fukuoka, Japan, December 1996.