Journal
GLYCOBIOLOGY
Volume 23, Issue 7, Pages 764-777Publisher
OXFORD UNIV PRESS INC
DOI: 10.1093/glycob/cwt016
Keywords
chondroitin; epimerase; glycosaminoglycan; glycosyltransferase; heparan sulfate; heparin; hyaluronan or hyaluronic acid; libraries; microfluidics; oligosaccharide; polysaccharide; sulfatase; sulfotransferase; synthase; UDP-sugar
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Funding
- National Institutes of Health [R01GM38060, GM090127, HL096972, HL062244, HL62244]
- National Science Foundation
- Oklahoma Center for Advancement of Science Technology
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Glycosaminoglycans (GAGs) are complex polysaccharides composed of hexosamine-containing disaccharide repeating units. The three most studied classes of GAGs, heparin/heparan sulfate, hyaluronan and chondroitin/dermatan sulfate, are essential macromolecules. GAGs isolated from animal and microbial sources have been utilized therapeutically, but naturally occurring GAGs are extremely heterogeneous limiting further development of these agents. These molecules pose difficult targets to construct by classical organic syntheses due to the long chain lengths and complex patterns of modification by sulfation and epimerization. Chemoenzymatic synthesis, a process that employs exquisite enzyme catalysts and various defined precursors (e.g. uridine 5'-diphosphosphate-sugar donors, sulfate donors, acceptors and oxazoline precursors), promises to deliver homogeneous GAGs. This review covers both theoretical and practical issues of GAG oligosaccharide and polysaccharide preparation as single molecular entities and in library formats. Even at this early stage of technology development, nearly monodisperse GAGs can be made with either natural or artificial structures.
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