Developments in the Chemical Synthesis of Heparin and Heparan Sulfate

Heparin and heparan sulfate represent key members of the glycosaminoglycan family of carbohydrates and underpin considerable repertoires of biological importance. As such, their efficiency of synthesis represents a key requirement, to further understand and exploit the H/HS structure‐to‐biological f...

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Published in:Chemical record Vol. 21; no. 11; pp. 3238 - 3255
Main Authors: Pongener, Imlirenla, O'Shea, Conor, Wootton, Hannah, Watkinson, Michael, Miller, Gavin J.
Format: Journal Article
Language:English
Published: United States Wiley Subscription Services, Inc 01.11.2021
Subjects:
Carbohydrates
Chemical Phenomena
Chemical synthesis
Construction
glycosaminoglycan
Glycosaminoglycans
glycosylation
Heparan sulfate
Heparin
Heparitin Sulfate
Oligosaccharides
Structure-function relationships
Sugar
Sulfates
Sulfation
carbohydrates
heparin
glycosylation
heparan sulfate
glycosaminoglycan
ISSN:1527-8999, 1528-0691, 1528-0691
Online Access:Get full text
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Summary:Heparin and heparan sulfate represent key members of the glycosaminoglycan family of carbohydrates and underpin considerable repertoires of biological importance. As such, their efficiency of synthesis represents a key requirement, to further understand and exploit the H/HS structure‐to‐biological function axis. In this review we focus on chemical approaches to and methodology improvements for the synthesis of these essential sugars (from 2015 onwards). We first consider advances in accessing the heparin‐derived pentasaccharide anticoagulant fondaparinux. This is followed by heparan sulfate targets, including key building block synthesis, oligosaccharide construction and chemical sulfation techniques. We end with a consideration of technological improvements to traditional, solution‐phase synthesis approaches that are increasingly being utilised. This review describes recent advances (2015 onwards) surrounding the chemical synthesis of heparin and heparan sulfate.
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ISSN:1527-8999
1528-0691
1528-0691
DOI:10.1002/tcr.202100173