Chemical Synthesis of Glycosaminoglycans

Glycosaminoglycans (GAGs) as one major part of the glycocalyx are involved in many essential biological cell processes, as well as in many courses of diseases. Because of the potential therapeutic application of GAG polymers, fragments, and also derivatives toward different diseases (e.g., heparin d...

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Bibliographic Details
Published in:Chemical reviews 2016-07, Vol.116 (14), p.8193-8255
Main Authors: Mende, Marco, Bednarek, Christin, Wawryszyn, Mirella, Sauter, Paul, Biskup, Moritz B, Schepers, Ute, Bräse, Stefan
Format: Article
Language:English
Subjects:
Chemical synthesis
Combinatorial Chemistry Techniques
Disaccharides - chemistry
Enzymes
Glycosaminoglycans - chemical synthesis
Glycosaminoglycans - chemistry
Glycosylation
Monosaccharides - chemistry
Polymers
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Summary:Glycosaminoglycans (GAGs) as one major part of the glycocalyx are involved in many essential biological cell processes, as well as in many courses of diseases. Because of the potential therapeutic application of GAG polymers, fragments, and also derivatives toward different diseases (e.g., heparin derivatives against Alzheimer’s disease), there is a continual growing demand for new chemical syntheses, which suffice the high claim to stereoselectivity and chemoselectivity. This Review summarizes the progress of chemical syntheses of GAGs over the last 10 years. For each class of the glycosaminoglycanshyaluronan (HA), heparan sulfate/heparin (HS/HP), chondroitin/dermatan sulfate (CS/DS), and keratan sulfate (KS)mainly novel glycosylation strategies, elongation sequences, and protecting group patterns are discussed, but also (semi)­automated syntheses, enzymatic approaches, and functionalizations of synthesized or isolated GAGs are considered.
ISSN:0009-2665
1520-6890
DOI:10.1021/acs.chemrev.6b00010