title: Synthesis of a small library of bivalent α-D-mannopyranosides for lectin cross-linking.
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.
authors.affiliation: PharmaQAM, Department of Chemistry, Université du Québec à Montréal, PO Box 8888, Succ. Centre-Ville, Montréal (Québec), Canada H3C 3P8.
authors.forename: Milan
authors.initials: M
authors.lastname: Bergeron-Brlek
authors.forename: Tze Chieh
authors.initials: TC
authors.lastname: Shiao
authors.forename: M Corazon
authors.initials: MC
authors.lastname: Trono
authors.forename: René
authors.initials: R
authors.lastname: Roy
mesh_terms: D001419:Bacteria; D001426:Bacterial Proteins / Q000737:chemistry* / Q000378:metabolism; D002236:Carbohydrate Conformation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003432:Cross-Linking Reagents; D019281:Dimerization; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000378:metabolism; D058116:Lewis Acids / Q000737:chemistry; D008358:Mannose / Q000138:chemical synthesis* / Q000378:metabolism; D010165:Palladium / Q000737:chemistry; D037121:Plant Lectins / Q000737:chemistry* / Q000378:metabolism; D010944:Plants; D011485:Protein Binding; D011975:Receptors, Mitogen / Q000737:chemistry / Q000378:metabolism; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000378:metabolism
chemical_list: D001426:Bacterial Proteins; D003432:Cross-Linking Reagents; D006001:Glycoconjugates; D058116:Lewis Acids; D037121:Plant Lectins; D011975:Receptors, Mitogen; D054852:Small Molecule Libraries; D010165:Palladium; D008358:Mannose