Synthesis of 5-thiomannose-containing oligomannoside mimics: binding abilities to concanavalin A

Bioorg Med Chem Lett. 1998 Jun 2;8(11):1297-300. doi: 10.1016/s0960-894x(98)00207-8.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Concanavalin A / chemistry*
  • Crystallography, X-Ray
  • Fluorescence Polarization
  • Hydrogen Bonding
  • Molecular Conformation
  • Molecular Mimicry
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Protein Binding
  • Sulfides / chemical synthesis*
  • Sulfides / chemistry
  • Thermodynamics

Substances

  • Oligosaccharides
  • Sulfides
  • oligomannoside
  • Concanavalin A