Synthesis of Oligomeric Mannosides and Their Structure‐Binding Relationship with Concanavalin A |
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| Authors: | Chen‐Wei Li Kai‐Wei Hon Bhaswati Ghosh Po‐Han Li Hsien‐Ya Lin Po‐Han Chan Prof Chun‐Hung Lin Prof Yu‐Chie Chen Prof Kwok‐Kong Tony Mong |
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| Affiliation: | 1. Applied Chemistry Department, National Chiao Tung University (NCTU), 1001, Ta Hsueh Road, Hsinchu (Taiwan), Fax: (+)886‐3‐5723764;2. Institute of Biological Chemistry, Academia Sinica, Academia Road Sec. 2, Nankang, Taipei 115, Taiwan.;3. Department of Chemistry, National Taiwan University, Taipei 116, Taiwan. |
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| Abstract: | Small glycodendrimers with α‐mannosyl ligands were synthesized by using copper‐catalyzed azide–alkyne coupling chemistry and some of these molecules were used as multivalent ligands to study the induction of concanavalin A (Con A) precipitation. The results showed that the monovalent mannose ligand could induce the precipitation of Con A. This unexpected finding initiated a series of studies to characterize the molecular basis of the ligand–lectin interaction. The atypical precipitation is found to be specific to the mannose, fluorescein moiety (FITC), and Con A. Apparently the mannose ligand binds to Con A through hydrogen‐bonding interactions, whereas the binding of FITC is mediated by hydrophobic forces. |
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| Keywords: | carbohydrates dendrimers glycopeptides multivalent effect precipitation |
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