title: Synthesis of 5-thiomannose-containing oligomannoside mimics: binding abilities to concanavalin A.
abstract: 5-Thiomannose-containing oligomannoside mimics, 5SMan alpha(1,6)Man, 5SMan alpha(1,3)Man, 5SMan alpha(1,6)¿Man alpha(1,3)Man¿, Man alpha(1,6)¿5SMan alpha(1,3)Man¿, and 5SMan alpha(1,6)¿5SMan alpha(1,3)Man¿, were synthesized. Dissociation constants for the binding of these mimics to concanavalin A (ConA) were determined by a fluorescence anisotropy inhibition assay. Comparison of these data with those of the natural oligomannosides and with a crystal structure of the trimannoside-ConA complex established that replacing a ring oxygen atom with a sulfur atom causes about 1 kcal/mol decrease in the binding free energy when the ring oxygen is recognized with a hydrogen bonding.
authors.affiliation: Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Yokohama, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Yuasa
authors.forename: S
authors.initials: S
authors.lastname: Matsuura
authors.forename: H
authors.initials: H
authors.lastname: Hashimoto
mesh_terms: D003208:Concanavalin A / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005454:Fluorescence Polarization; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D018716:Molecular Mimicry; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011485:Protein Binding; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry; D013816:Thermodynamics
chemical_list: D009844:Oligosaccharides; D013440:Sulfides; C028569:oligomannoside; D003208:Concanavalin A