Chiral discrimination of permethylated gluco-oligosaccharide toward amino acid ester salts

Tetrahedron

Volumn 57, Issue 21, 2001, Pages 4567-4578

  Shizuma, Motohiro ^a   Adachi, Hiroshi ^b   Amemura, Akinori ^c   Takai, Yoshio ^d   Takeda, Tokuji ^a   Sawada, Masami ^d  

^a OSAKA MUNICIPAL TECHNICAL RESEARCH INSTITUTE   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c FUKUYAMA UNIVERSITY   (Japan)

^d Osaka University   (Japan)

Author keywords

Amino acids and derivatives; Carbohydrate; Enantioselection; Molecular recognition

Indexed keywords

ALPHA CYCLODEXTRIN; AMINO ACID DERIVATIVE; BETA CYCLODEXTRIN; ESTER DERIVATIVE; OLIGOSACCHARIDE; TRYPTOPHAN;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; MASS SPECTROMETRY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0035927194     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)00390-8     Document Type: Article

References (34)

1. Díhulst A., Berbeke N. Chirality. 6:1994;225-229.
2. Yashima E., Okamoto Y. Bull. Chem. Soc. Jpn. 68:1995;3289-3307.
3. Yashima E., Yamamoto C., Okamoto Y. J. Am. Chem. Soc. 118:1996;4036-4048.
4. Okamoto Y., Yashima E. Angew. Chem. Int. Ed. Engl. 37:1998;1020-1043.
5. Soini H., Stefansson M., Riekkola M.-L., Novotny M.V. Anal. Chem. 66:1994;3477-3484.
6. Kano K., Minami K., Horiguchi K., Ishimura T., Kodera M. J. Chromatogr. A. 694:1995;307-313.
7. Kano K., Negi S., Takaoka R., Kamo H., Kitae T., Yamaguchi M., Okubo H., Hirama M. Chem. Lett. 1997;715-716.
8. We have found few reports for the enantioselective formation of 1:1 complexes of linear oligosaccharides with chiral compounds until now. In the case of β-cyclodextrin, see: Rekharsky M., Inoue Y. J. Am. Chem. Soc. 122:2000;4418-4435.
9. Sawada M., Shizuma M., Takai Y., Adachi H., Takeda T., Uchiyama T. Chem. Commun. 1998;1453-1454.
10. Sawada M., Takai Y., Yamada H., Hirayama S., Kaneda T., Tanaka T., Kamada K., Mizooku T., Takeuchi S., Ueno K., Hirose K., Tobe Y., Naemura K. J. Am. Chem. Soc. 117:1995;7726-7736.
11. Sawada M. Mass Spectrom. Rev. 16:1997;73-90.
12. Sawada M. J. Mass Spectrom. Soc. Jpn. 45:1997;439-458.
13. Shizuma M. J. Mass. Spectrom. Soc. Jpn. 46:1998;211-218.
14. S-dx<1.0, S-selectivity.
15. Sawada M., Takai Y., Yamada H., Nishida J., Kaneda T., Arakawa R., Okamoto M., Hirose K., Tanaka T., Naemura K. J. Chem. Soc., Perkin Trans. 2. 1998;701-710.
16. Lipkowitz K.B., Raghothama S., Yang J.-a. J. Am. Chem. Soc. 114:1992;1554-1562.
17. Takai Y., Okumura Y., Sawada M., Takahashi S., Siro M., Kawamura M., Uchiyama T. J. Org. Chem. 59:1994;2967-2975.
18. Live D., Chan S.I. J. Am. Chem. Soc. 98:1976;3769.
19. Nishio M. Tetrahedron. 51:1995;8665.
20. Nishio M. Bull. Chem. Soc. Jpn. 71:1998;1207.
21. Suzuki Y., Morozumi T., Nakamura H., Shimomura M., Hayashita T., Bartsh R.A. J. Phys. Chem. B. 102:1998;7910-7917.
22. Otsuki J., Kobayashi K., Toi H., Aoyama Y. Tetrahedron Lett. 34:1993;1945-1948.
23. Pirkle W.H., Pochapsky T.C. Chem. Rev. 89:1989;347-362.
24. Nishio M., Hirota M. Tetrahedron. 45:1989;7201.
25. Hakomori S. J. Biochem. (Tokyo). 55:1964;205-208.
26. Conard H.E. Whister R.L., Bemiller S.N. Method in Carbohydrate Chemistry. 6:1972;361 Academic Press, New York.
27. Melton L.D., McNeil M., Darvill A.G., Albersheim P., Dell A. Carbohydr. Res. 146:1986;279.
28. Amemura A., Moori K., Harada T. Biochim. Biophys. Acta. 334:1974;398-409.
29. Kyba E.P., Timko J.M., Kaplan L.J., de Jong F., Gokel G.W., Cram D.J. J. Am. Chem. Soc. 100:1978;4555-4568.
30. Todd J.S., Proteau P.J., Gerwick W.H. Tetrahedron Lett. 34:1993;7685-7688.
31. Sun H., Ren P., Fried J.P. Computational and Theoretical Polymer Science. 1998;229-246.
32. Hoover W.G. Computational Statistical Mechanics. 1990;Elsevier, Amsterdam.
33. Tone K. BASIC. 1981;137-146 Baifukan. chap. 28.
34. Tsukube H., Sohmiya H. J. Org. Chem. 56:1991;875.