Synthesis of 5-thiomannose-containing oligomannoside mimics: binding abilities to concanavalin A.
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.
Yuasa
H
H
Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Yokohama, Japan.
Matsuura
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S
Hashimoto
H
H
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
D009844:Oligosaccharides; D013440:Sulfides; C028569:oligomannoside; D003208:Concanavalin A