Crystal and molecular structures of diglycosyl disulfide derivatives

Carbohydr Res. 2006 Dec 29;341(18):2967-72. doi: 10.1016/j.carres.2006.10.018. Epub 2006 Oct 25.

Abstract

The crystal and molecular structures of S-(2,3,4,6-tetra-O-acetyl-beta-d-glucopyranosyl)-S'-(2,3,4,6-tetra-O-acetyl-beta-d-galactopyranosyl)disulfide (1) and the mono-sulfoxide (3) of bis(2,3,4,6-tetra-O-acetyl-beta-d-glucopyranosyl)disulfide (2) are described. Comparison of 2 and 3, containing -S-S- and -S-S(O)- bonds, respectively, allows to delineate structural differences brought about by the different oxidation states of one of the sulfur atoms in carbohydrate disulfides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallization
  • Crystallography, X-Ray
  • Disulfides / chemistry*
  • Sulfoxides / chemistry
  • Thioglycosides / chemistry*

Substances

  • Disulfides
  • S-(2,3,4,6-tetra-O-acetylglucopyranosyl)-S'-(2,3,4,6-tetra-O--acetylgalactopyranosyl)disulfide S-oxide
  • S-(2,3,4,6-tetra-O-acetylglucopyranosyl)-S'-(2,3,4,6-tetra-O-acetylgalactopyranosyl)disulfide
  • Sulfoxides
  • Thioglycosides