Structure and ethanol complexation of cyclic tetrasaccharide in aqueous solution studied by NMR and molecular mechanics

Chemical and Pharmaceutical Bulletin

Volumn 52, Issue 6, 2004, Pages 708-713

  Funasaki, Noriaki ^a   Ishikawa, Seiji ^a   Hirota, Shun ^a   Neya, Saburo ^b   Nishimoto, Tomoyuki ^c  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

^c HAYASHIBARA BIOCHEMICAL LABORATORIES INC   (Japan)

Author keywords

Cyclic tetrasaccharide; Ethanol binding; Molecular mechanics; NMR; Solution structure

Indexed keywords

ALCOHOL; CARBOHYDRATE DERIVATIVE; CYCLODEXTRIN DERIVATIVE; GLUCOSE; PROTON; WATER; CYCLIC TETRASACCHARIDE, BACILLUS GLOBISPORUS; OLIGOSACCHARIDE;

ADSORPTION; AQUEOUS SOLUTION; ARTICLE; CALCULATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); CORRELATION ANALYSIS; CRYSTAL STRUCTURE; MOLECULAR MECHANICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SIMULATION; X RAY CRYSTALLOGRAPHY; BINDING SITE; CHEMISTRY; METABOLISM; METHODOLOGY; SOLUTION AND SOLUBILITY;

BINDING SITES; ETHANOL; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OLIGOSACCHARIDES; SOLUTIONS; WATER;

EID: 13244275950     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.52.708     Document Type: Article

References (27)

1. Bender M. L., Komiyama M., "Cyclodextrin Chemistry," Chapters 2 and 3, Springer-Verlag, Berlin, 1978.
2. Szejtli J., "Cyclodextrin Technology," Chapters 2 and 3, Kluwer Academic Publishers, Dordrecht, The Netherlands, 1988.
3. Côte G. L., Biely P., Eur. J. Biochem., 226, 641-648 (1994).
4. Miller K. J., Gore R. S., Johnson R., Benesi A. J., Reinhold V. N., J. Bacteriol., 172, 136-142 (1990).
5. Gattuso G., Nepogodiev S. A., Stoddart J. F., Chem. Rev., 98, 1977-1996 (1998).
6. Nishimoto T., Aga H., Mukai K., Hashimoto T., Watanabe H., Kubota M., Fukuda S., Kurimoto M., Tsujisaka Y., Biosci. Biotechnol. Biochem., 66, 1806-1818 (2002).
7. Bradbrook G. M., Gessler K., Côte G. L., Momany F. A., Biely P., Bordet P., Perez S., Imberty A., Carbohydr. Res., 329, 655-665 (2000).
8. Križ Z., Koča J., Imberty A., Charlot A., Auzély-Velty R., Org. Biomol. Chem., 1, 2590-2595 (2003).
9. Schneider H.-J., Hacket F., Rüdiger V., Ikeda H., Chem. Rev., 98, 1755-1785 (1998).
10. Hedges A. R., Chem. Rev., 98, 2035-2044 (1998).
11. Funasaki N., Yamaguchi H., Ishikawa S., Neya S., J. Phys. Chem. B, 105, 760-765 (2001).
12. Hada S., Neya S., Funasaki N., J. Phys. Chem. B, 103, 2579-2584 (1999).
13. Funasaki N., Nomura M., Ishikawa S., Neya S., J. Phys. Chem. B, 105, 7361-7365 (2001).
14. Funasaki N., Nomura M., Yamaguchi H., Ishikawa S., Neya S., Bull. Chem. Soc. Jpn., 73, 2727-2728 (2000).
15. Bonas G., Vignon M., Rec. Trav. Chim. Pays-Bas, 108, 161-162 (1989).
16. Dunlap C. A., Côte G. L., Momany F. A., Carbohydr. Res., 338, 2367-2373 (2003).
17. Kessler H., Seip S., "Two-dimensional NMR Spectroscopy," 2nd ed., Chapter 5, ed. by Croasmun W. R., Carlson R. M. K., Wiley-VCH, New York, 1994.
18. Neuhaus D., Williamson M. P., "The Nuclear Overhauser Effect in Structural and Conformational Analysis," 2nd ed., Chapters 5, 9 and 12, Wiley-VCH, New York, 2000.
19. Glaros G., Cromwell N. H., J. Chem. Educ., 48, 202-203 (1971).
20. Gelb R. I., Schwartz L. M., Radeos M., Edmonds R. B., Laufer D. A., J. Am. Chem. Soc., 104, 6283-6288 (1982).
21. Barrow G. M., "Physical Chemistry for the Life Sciences," Chapter 6, McGraw-Hill, London, 1981.
22. Tanford C., "Physical Chemistry of Macromolecules," Chapter 8, John Wiley and Sons, New York, 1961.
23. Mortimer R. G., "Mathematics for Physical Chemistry," Chapter 9, Macmillan, New York, 1981.
24. Claridge T. D. W., "High-Resolution NMR Techniques in Organic Chemistry," Chapter 8, Pergamon, Oxford, 1999.
25. Hull W. E., "Two-dimensional NMR Spectroscopy," 2nd ed., Chapter 2, ed. by Croasmun W. R., Carlson R. M. K., Wiley-VCH, New York, 1994.
26. Funasaki N., Yamaguchi H., Ishikawa S., Neya S., J. Phys. Chem. B, 104, 10412-10418 (2000).
27. Bonas G., Vignon M. R., Pérez S., Carbohydr. Res., 211, 191-205 (1991).