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Recent Chemical and Enzymatic Approaches to the Synthesis of Glycosaminoglycan Oligosaccharides

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Abstract:

Glycosaminoglycans, highly charged polycarboxylated, polysulfated polysaccharides, are an important class of therapeutic agents and investigational drug candidates. Heparin has been widely used as a clinical anticoagulant for over 60 years. Low molecular weight heparins have begun to displace heparin and recently a synthetic heparin pentasaccharide was approved for clinical use in Europe. In addition to heparin (and the related heparan sulfate glycosaminoglycan), dermatan sulfate, chondroitin sulfate, hyaluronan and their derivatives are all in various stages of clinical evaluation. This review focuses on the chemical and chemoenzymatic synthesis of glycosaminoglycan oligosaccharides. Recent advances in functional group protection chemistry, conversion of D-gluco to L-ido or D-galacto configurations, glycosylation reactions and the preparation and use of novel starting materials in acidic oligosaccharide synthesis are discussed.

Keywords: chondroitin sulfate; dermatan sulfate; enzymatic synthesis; glycosaminoglycans; heparan sulfate; heparin; hyaluronic acid; oligosaccharide synthesis

Document Type: Review Article

DOI: https://doi.org/10.2174/0929867033456891

Affiliations: Division of Medicinal and Natural Products Chemistry, Department of Chemistry and Department of Chemical and Biochemical Engineering, University of Iowa, Iowa City, Iowa, 52242, USA.

Publication date: 2003-10-01

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  • Current Medicinal Chemistry covers all the latest and outstanding developments in medicinal chemistry and rational drug design. Each issue contains a series of timely in-depth reviews written by leaders in the field covering a range of the current topics in medicinal chemistry. Current Medicinal Chemistry is an essential journal for every medicinal chemist who wishes to be kept informed and up-to-date with the latest and most important developments.
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