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Glycobiology Advance Access published online on May 11, 2005
Glycobiology, doi:10.1093/glycob/cwi074
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© The Author 2005. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oupjournals.org
Received March 16, 2005
Revised May 3, 2005
Accepted May 5, 2005

Article

Banana lectin is unique in its recognition of the reducing unit of 3-O-{beta}-glucosyl/mannosyl disaccharides. A calorimetric study

Harry C. Winter 1, Stefan Oscarson 2, Rikard Slättegård 2, Maozhong Tian 2, and Irwin J. Goldstein 1*

1 Department of Biological Chemistry, The University of Michigan Medical School, Ann Arbor, Mi, USA
2 Department of Organic Chemistry, University of Stockholm, S-10691 Stockholm, Sweden


  Abstract

The binding of banana lectin (BanLec) to laminaribiose (Glc{beta}1,3Glc) and a series of novel synthetic analogues was measured by titration calorimetry to assess the contribution of the hydroxyl groups of the reducing glycosyl moiety and its 3-O-{beta}-substituent to binding. Key areas of interaction involved the 1, 2, and 6 positions of the reducing-terminal hexose unit. The {alpha}-anomeric configuration of the reducing hexose was strongly favored over the {beta}-anomer. The 2-hydroxyl in the axial position (mannose) also enhanced binding, whereas the 6-hydroxymethyl group was essential, since xylopyranose in the reducing position was inactive. The 3-O-{beta}-glucosyl unit of methyl {alpha}-laminaribioside could be replaced by any of its monodeoxy derivatives. However, the 4'-deoxy derivative or axial hydroxy (galactosyl) substitution was somewhat detrimental to binding. 3-O-substitution with the (S)tetrahydropyranyl ring or a benzyl group had similar effect as 4'-deoxyglucosyl substitution. Surprisingly, p-nitrobenzyl or {beta}-xylosyl 3-O-substitution greatly enhanced binding of the reducing glucosyl or mannosyl derivative. Chemical syntheses of a number of novel disaccharides and analogues prepared for this study are described.

Keywords: Calorimetric titration, carbohydrate recognition, glucose/mannose lectin, glycosynthesis, laminaribiose.
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