title: Synthesis of oligomeric mannosides and their structure-binding relationship with concanavalin A.
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.
authors.affiliation: Applied Chemistry Department, National Chiao Tung University (NCTU), 1001, Ta Hsueh Road, Hsinchu (Taiwan), Fax: (+)886-3-5723764.
authors.forename: Chen-Wei
authors.initials: CW
authors.lastname: Li
authors.forename: Kai-Wei
authors.initials: KW
authors.lastname: Hon
authors.forename: Bhaswati
authors.initials: B
authors.lastname: Ghosh
authors.forename: Po-Han
authors.initials: PH
authors.lastname: Li
authors.forename: Hsien-Ya
authors.initials: HY
authors.lastname: Lin
authors.forename: Po-Han
authors.initials: PH
authors.lastname: Chan
authors.forename: Chun-Hung
authors.initials: CH
authors.lastname: Lin
authors.forename: Yu-Chie
authors.initials: YC
authors.lastname: Chen
authors.forename: Kwok-Kong Tony
authors.initials: KK
authors.lastname: Mong
mesh_terms: D001665:Binding Sites; D011232:Chemical Precipitation; D060326:Chemistry Techniques, Synthetic; D003208:Concanavalin A / Q000737:chemistry / Q000378:metabolism*; D019793:Fluorescein / Q000737:chemistry / Q000378:metabolism; D005454:Fluorescence Polarization; D008362:Mannosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D012542:Scattering, Radiation; D013329:Structure-Activity Relationship; D013816:Thermodynamics
chemical_list: D008362:Mannosides; D003208:Concanavalin A; D019793:Fluorescein
keywords: carbohydrates; dendrimers; glycopeptides; multivalent effect; precipitation