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Structure of the Chondroitin 4-Sulfate-Protein Linkage Region

ISOLATION AND CHARACTERIZATION OF THE DISACCHARIDE 3-O--d-GLUCURONOSYL-d-GALACTOSE

From the ¹ From the La Rabida-University of Chicago Institute and the Department of Biochemistry, University of Chicago, Chicago, Illinois 60649

A disaccharide composed of glucuronic acid and d-galactose has been isolated from chondroitin 4-sulfate and chondroitin 4-sulfate glycopeptides. Its structure has been determined in the following way. (a) Reduction with borohydride demonstrated that galactose constitutes the reducing end of the disaccharide; (b) digestion with ß-glucuronidase cleaved the disaccharide into glucuronic acid and galactose, demonstrating a ß linkage; (c) periodate oxidation of the disaccharide methylglycoside resulted in no loss of galactose; and (d) oxidation of the disaccharide with lead tetraacetate degraded the galactose moiety to lyxose. This establishes the structure of the disaccharide as 3-O-ß-d-glucuronosyl-d-galactose.

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