The synthesis of a novel thio-linked disaccharide of chondroitin as a potential inhibitor of polysaccharide lyases

Carl S Rye; Stephen G Withers

doi:10.1016/j.carres.2003.12.011

The synthesis of a novel thio-linked disaccharide of chondroitin as a potential inhibitor of polysaccharide lyases

Carbohydr Res. 2004 Feb 25;339(3):699-703. doi: 10.1016/j.carres.2003.12.011.

Authors

Carl S Rye¹, Stephen G Withers

Affiliation

¹ Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, BC, Canada V6T 1Z1.

PMID: 15013408
DOI: 10.1016/j.carres.2003.12.011

Abstract

A thio-linked disaccharide based on the structure of the glycosaminoglycan chondroitin was synthesized as a potential inhibitor of chondroitin AC lyase from Flavobacterium heparinum for structural analysis of the active site. Instead it was found to be a slow substrate, thereby demonstrating that lyases, in contrast to glycosidases, can cleave thioglycoside links between sugars.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Sequence
Chondroitin / chemical synthesis*
Chondroitin / chemistry
Chondroitin / pharmacology*
Disaccharides / chemical synthesis
Disaccharides / chemistry*
Disaccharides / pharmacology
Flavobacterium / enzymology
Kinetics
Molecular Structure
Polysaccharide-Lyases / antagonists & inhibitors*
Polysaccharide-Lyases / metabolism
Sulfhydryl Compounds / chemistry*

Substances

Disaccharides
Sulfhydryl Compounds
Chondroitin
Polysaccharide-Lyases