Chondroitin

Preparation of the methyl ester of hyaluronan and its enzymatic degradation.

Hirano K, Sakai S, Ishikawa T, Avci FY, Linhardt RJ, Toida T.

Graduate School of Pharmaceutical Sciences, Chiba University, 1-33, Inage-ku, Chiba-shi, Chiba 263-8522, Japan.

A methyl ester of hyaluronan in which the carboxyl groups were fully esterified was prepared using trimethylsilyl diazomethane. This derivative, while not depolymerized by hyaluronan lyases or hyaluronan hydrolases, was a substrate for both chondroitin ACI lyase (EC 4.2.2.5) from Flavobacterium heparinum and chondroitin ACII lyase (EC 4.2.2.5) from Arthrobacter aurescens. The major product isolated in these depolymerization reactions was methyl alpha-L-threo-hex-4-enepyranosyluronate-(1-->3)-2-acetamido-2-deoxy-alpha,beta-D-glucopyranoside as determined by 1H NMR spectroscopy and MALDITOF mass spectrometry.

PMID: 16098492 [PubMed - indexed for MEDLINE]

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