Glycobiology Advance Access originally published online on May 11, 2005
Glycobiology 2005 15(10):1043-1050; doi:10.1093/glycob/cwi074
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Banana lectin is unique in its recognition of the reducing unit of 3-O-ß-glucosyl/mannosyl disaccharides: a calorimetric study
2 Department of Biological Chemistry, The University of Michigan Medical School, Ann Arbor, MI; and 3 Department of Organic Chemistry, University of Stockholm, S-10691 Stockholm, Sweden
1 To whom correspondence should be addressed; e-mail: igoldste{at}umich.edu
Received on March 16, 2005; revised on May 3, 2005; accepted on May 5, 2005
The binding of banana lectin (BanLec) to laminaribiose (Glcß1,3Glc) 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-ß-substituent to binding. Key areas of interaction involved the 1, 2, and 6 positions of the reducing-terminal hexose unit. The 
-anomeric configuration of the reducing hexose was strongly favored over the ß-anomer. The 2-hydroxyl in the axial position (mannose) also enhanced binding, whereas the 6-hydroxymethyl group was essential, because xylopyranose in the reducing position was inactive. The 3-O-ß-glucosyl unit of methyl -laminaribioside could be replaced by any of its monodeoxy derivatives. However, the 49-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 49-deoxyglucosyl substitution. Surprisingly, p-nitrobenzyl or ß-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.
Key words: calorimetric titration / carbohydrate recognition / glucose-binding lectin / glycosynthesis / laminaribiose
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