Saccharide Induction of Chiral Orientation of the Aggregate Formed from Boronic-Acid-Appended Amphiphiles

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 9, 1998, Pages 2197-2204

  Kimura, Taro ^a   Takeuchi, Masayuki ^a   Shinkai, Seiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000522404     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.2197     Document Type: Article

References (47)

1. a) M. Nakamura, K Kirito, J. Yamanoi, T. Wainai, H. Nojiri, and M. Saito, Cancer Res., 51, 1940 (1991);
2. b) P. J. Quinn and W. P. Williams, Biochim. Biophys. Acta, 737, 223 (1983).
3. a) Y. Aoyama, Y. Tanaka, H. Toi, and H. Ogoshi, J. Am. Chem. Soc., 110, 634 (1988);
4. b) Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989);
5. Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
6. a) N. Nakashima, S. Asakuma, and T. Kunitake, J. Chem. Soc., Perkin Trans. 2, 1991, 885;
7. b) N. Nakashima, S. Asakuma, J-M. Kim, and T. Kunitake, Chem. Lett., 1984, 1709;
8. T. Kunitake and N. Yamada, J. Chem. Soc., Chem. Commun., 1986, 655;
9. T. Kunitake, J-M. Kim, and Y. Ishikawa, J. Chem. Soc., Perkin Trans. 2, 1991, 885.
10. a) T. Shimizu and M. Hato, Biochim. Biophys. Acta, 1993, 50;
11. b) T. Shimizu and M. Masuda, J. Am. Chem. Soc., 119, 2812 (1997).
12. a) J.-H. Fuhrhop, P. Schnieder, J. Rosenberg, and E. Boekema, J. Am. Chem. Soc., 109, 3387 (1987);
13. b) J.-H. Fuhrhop, S. Svenson, C. Boettcher, E. Rossler, and H.-M. Vieth, J. Am. Chem. Soc., 112, 4307 (1990).
14. a) K. Murata, M. Aoki, T. Suzuki, T. Harada, H. Kawabata, T. Komori, F. Ohseto, K. Ueda, and S. Shinkai, J. Am. Chem. Soc., 116, 6664 (1994), and references cited therein;
15. b) T. D. James, K. Murata, T. Harada, K. Ueda, and S. Shinkai, Chem. Lettt., 1994, 273.
16. a) K. Hanabusa, M. Yamada, M. Kimura, and H. Hirai, Angew. Chem., Int. Ed. Engl., 35, 1949 (1996);
17. b) N. Sommerdijk, M. Lambermon, M. Feiters, R. Nolte, and B. Zwanenburg, J. Chem. Soc., Chem. Commun., 1997, 1423;
18. R. Hafkamp, B. Kokke, I. Danke, H. Geurts, A. Rowan, M. Feiters, and R. Nolte, J. Chem. Soc., Chem. Commun., 1997, 545.
19. a) Y. Shiomi, M. Saisho, K. Tsukagoshi, and S. Sinkai, J. Chem. Soc., Perkin Trans. 1, 1993, 2111;
20. b) T. D. James, K. R. A. S. Sandanayake, and S. Shinkai, Angew. Chem., Int. Ed. Engl., 33, 2207 (1994);
21. T. Imada, H. Murakami, and S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 1557;
22. T. Kimura, S. Arimori, M. Takeuchi, T. Nagasaki, and S. Shinkai, J. Chem. Soc., Perkin Trans. 2, 1995, 1889;
23. e) T. Nagasaki, H. Shinmori, and S. Shinkai, Tetrahedron. Lett., 35, 2201 (1994).
24. For comprehensive reviews see following articles: a) T. D. James, K. R. A. S. Sandanayake, and S. Shinkai, Supramol. Chem., 6, 141 (1995); b) T. D. James, K. R. A. S. Sandanayake, and S. Shinkai, Angew. Chem., Int. Ed. Engl., 35, 1910 (1996).
25. For comprehensive reviews see following articles: a) T. D. James, K. R. A. S. Sandanayake, and S. Shinkai, Supramol. Chem., 6, 141 (1995); b) T. D. James, K. R. A. S. Sandanayake, and S. Shinkai, Angew. Chem., Int. Ed. Engl., 35, 1910 (1996).
26. J. Yoon and A. W. Czarnik, J. Am. Chem. Soc., 114, 5874 (1992).
27. a) H. Toi, Y. Nagai, Y. Aoyama, H. Kawabe, K. Aizawa, and H. Ogoshi, Chem. Lett., 1993, 1043 (1993);
28. b) Y. Nagai, K. Kobayashi, H. Toi, and Y. Aoyama, Bull. Chem. Soc. Jpn., 66, 2965 (1993).
29. a) M. F. Paugam, G. T. Morin, and B. D. Smith, Tetrahedron Lett., 34, 7841 (1993);
30. b) M. F. Paugam and B. D. Simth, Tetrahedron Lett., 34, 3723 (1993);
31. G. T. Morin, M. P. Hughes, M. F. Paugam, and B. D. Smith, J. Am. Chem. Soc., 116, 8895 (1994);
32. P. R. Westmark and B. D. Smith, J. Am. Chem. Soc., 116, 9343 (1994);
33. e) M. F. Paugam, L. S. Valencia, B. Boggess, and B. D. Smith, J. Am. Chem. Soc., 116, 11203 (1994).
34. J.-H. Fuhrhop, C. Demoulin, C. Boettcher, J. Koning, and U. Siggel, J. Am. Chem. Soc., 114, 4159 (1992).
35. S. Arimori, M. Takeuchi, and S. Shinkai, J. Am. Chem. Soc., 118, 245 (1996).
36. T. Kimura, M. Takeuchi, I. Hamachi, and S. Sinkai, Isr. J. Chem., 36, 379 (1996).
37. M. Takeuchi, K. Koumoto, M. Goto, and S. Shinkai, Tetrahedron, 52, 12931 (1996).
38. T. Kunitake, Angew. Chem., Int. Ed. Engl., 31, 709 (1992), and references cited therein.
39. J. P. Lorand and J. O. Edwards, J. Org. Chem., 24, 769 (1959).
40. K. Nakanishi, N. Berova, and R. W. Woody, "Circular Dichroism Principles and Applications," VCH Publishers, Inc., New York (1994), pp. 361-365.
41. a) S. Shinkai, K. Tsukagoshi, Y. Ishikawa, and T. Kunitake, J. Chem. Soc., Chem. Commun., 1991, 1039;
42. b) T. D. James, S. Sandanayake, R. Iguchi, and S. Shinkai, J. Am. Chem. Soc., 117, 8982 (1995);
43. M. Mikami and S. Shinkai, J. Chem. Soc., Chem. Commun., 1995, 153.
44. J. C. Norrild and H. Eggert, J. Am. Chem. Soc., 117, 1479 (1995).
45. R. Ludwig, K. Ariga, and S. Shinkai, Chem. Lett., 1993, 1413.
46. J. C. Norrild and H. Eggert, J. Chem. Soc., Perkin Trans. 2, 1996, 2853.
47. H. Shinmori, M. Takeuchi, and S. Shinkai, Tetrahedron, 51, 1893 (1995).