Abstract
A small library of bivalent α-D-mannopyranosides having rigid linkers was constructed in order to evaluate the effects of inter-saccharide distances upon multivalent binding interactions with plant and bacterial lectins. To this end, iodoaryl and propargyl α-D-mannopyranosides were synthesized and the former treated with TMS-acetylene under palladium chemistry to provide their corresponding ethynylaryl derivatives. A library of 15 dimeric members was then obtained using Lewis acid catalyzed glycosidation, aryl-aryl homocoupling, transition metal catalyzed Sonogashira cross-coupling reactions, and oxidative Glaser homocoupling.
Copyright © 2011 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Bacteria
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Bacterial Proteins / chemistry*
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Bacterial Proteins / metabolism
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Carbohydrate Conformation
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Catalysis
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Combinatorial Chemistry Techniques / methods*
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Cross-Linking Reagents
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Dimerization
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Glycoconjugates / chemical synthesis*
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Glycoconjugates / metabolism
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Lewis Acids / chemistry
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Mannose / chemical synthesis*
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Mannose / metabolism
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Palladium / chemistry
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Plant Lectins / chemistry*
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Plant Lectins / metabolism
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Plants
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Protein Binding
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Receptors, Mitogen / chemistry
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Receptors, Mitogen / metabolism
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Small Molecule Libraries / chemical synthesis*
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Small Molecule Libraries / metabolism
Substances
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Bacterial Proteins
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Cross-Linking Reagents
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Glycoconjugates
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Lewis Acids
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Plant Lectins
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Receptors, Mitogen
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Small Molecule Libraries
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Palladium
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Mannose