The crystal structure of 1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranose: Observation of C-H⋯π interaction as a surrogate to O-H⋯O interaction of a free sugar

Carbohydrate Research

Volumn 338, Issue 19, 2003, Pages 2005-2011

  Muktha, B ^a   Srinivas, O ^a   Amresh, M R ^a   Guru Row, T N ^a   Jayaraman, N ^a   Sekar, K ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

C H interaction; Conformation; Crystal structures; Hydrogen bonding; Pyranose; D Mannose

Indexed keywords

BENZENE; CONFORMATIONS; CRYSTAL STRUCTURE; SUPRAMOLECULAR CHEMISTRY; X RAY CRYSTALLOGRAPHY;

SUPRAMOLECULAR ORGANIZATION;

SUGARS;

1,2,3,4,6 PENTA O BENZOYL ALPHA DEXTRO MANNOPYRANOSE; CARBOHYDRATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; CRYSTAL STRUCTURE; HYDROGEN BOND; MOLECULAR INTERACTION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0142090498     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(03)00340-9     Document Type: Article

References (27)

1. Jeffrey G.A., Saenger W. Hydrogen Bonding in Biological Structures. 1991;Springer, Berlin.
2. Steiner T., Saenger W. Carbohydr. Res. 259:1994;1-12.
3. Ceccarelli C., Jeffrey G.A., Taylor R. J. Mol. Struct. 70:1981;255-271.
4. Jeffrey G.A., Mitra J. Acta Crystallogr. B39:1983;469-480.
5. Desiraju G.R., Steiner T. The Weak Hydrogen Bond in Structural Chemistry and Biology. 1999;Oxford University Press, Oxford.
6. Nishio M., Hirota M., Umezawa Y. The CH/π Interaction: Evidence, Nature and Consequences. 1998;Wiley-VCH, New York.
7. Kishikawa K., Yoshizaki K., Kohmoto S., Yamamoto M., Yamaguchi K., Yamada K. J. Chem. Soc. Perkin Trans. 1. 1997;1233-1240.
8. Suezawa H., Hashimoto T., Tsuchinaga K., Yoshida T., Yuzuri T., Sakakibara K., Hirota M., Nishio M. J. Chem. Soc. Perkin Trans. 2. 2000;1243-1249.
9. Madhavi N.N.L., Katz A.K., Carrell H.L., Nangia A., Desiraju G.R. Chem. Commun. 1997;1953-1954.
10. Kobayashi K., Asakawa Y., Aoyama Y. Supramol. Chem. 2:1993;133.
11. Tsuzuki S., Honda K., Uchimaru T., Mikami M., Tanabe K. J. Am. Chem. Soc. 122:2000;3746-3753.
12. Kim E.I., Paliwal S., Wilcox C.S. J. Am. Chem. Soc. 120:1998;11192-11193.
13. Steiner T. J. Chem. Soc. Chem. Commun. 1995;95-96.
14. Hunter C.A., Lawson K.R., Perkins J., Urch C.J. J. Chem. Soc. Perkin Trans. 2. 2001;651-669.
15. Umezawa Y., Tsubuyama S., Honda K., Uzawa J., Nishio M. Bull. Chem. Soc. Jpn. 71:1998;1207-1213.
16. Ness R.K., Fletcher H.G. Jr., Hudson C.S. J. Am. Chem. Soc. 72:1950;2200-2205.
17. Bruker SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA, 1998.
18. Sheldrick, G.M. SHELXS97 and SHELXL97. University of Göttingen, Germany, 1997.
19. Berman H.M., Chu S.S.C., Jeffrey G.A. Science. 157:1967;1576-1577.
20. Longchambon F., Neuman A. Acta Crystallogr. B32:1976;1822-1826.
21. Cremer D., Pople J.A. J. Am. Chem. Soc. 97:1975;1354-1358.
22. Jeffrey G.A. Acta Crystallogr. B46:1990;89-103.
23. Jeffrey G.A., Yates J.H. Carbohydr. Res. 74:1979;319-322.
24. Stoddart J.F. Stereochemistry of Carbohydrates. 1971;Wiley, New York.
25. Takahashi H., Tsuboyama S., Umezawa Y., Honda K., Nishio M. Tetrahedron. 56:2000;6185-6191.
26. Nardelli L.J. Appl. Crystallogr. 28:1995;659.
27. Broder C.K., Howard J.A.K., Keen D.A., Wilson C.C., Allen F.H., Jetti R.K.R., Nangia A., Desiraju G.R. Acta Crystallogr. B56:2000;1080-1084.