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Issue 32, 2018
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Programmable one-pot synthesis of heparin pentasaccharides enabling access to regiodefined sulfate derivatives

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Abstract

Heparin (H) and heparan sulfate (HS) belong to the glycosaminoglycan (GAG) family of oligosaccharides, and their sequences and sulfation patterns are known to regulate the functions of various proteins in biological processes. Among these, the 6-O-sulfation of HS/H contributes most significantly to the structural diversity and binding interactions. However, the synthesis of HS with defined sulfation patterns remains a major challenge. Herein, we report a highly efficient and programmable one-pot method for the synthesis of protected heparin pentasaccharides using thioglycoside building blocks with optimized relative reactivities to allow the selective deprotection and preparation of regiodefined sulfate derivatives.

Graphical abstract: Programmable one-pot synthesis of heparin pentasaccharides enabling access to regiodefined sulfate derivatives

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Publication details

The article was received on 17 Apr 2018, accepted on 01 Jul 2018 and first published on 03 Jul 2018


Article type: Edge Article
DOI: 10.1039/C8SC01743C
Citation: Chem. Sci., 2018,9, 6685-6691
  • Open access: Creative Commons BY-NC license
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    Programmable one-pot synthesis of heparin pentasaccharides enabling access to regiodefined sulfate derivatives

    S. Dey and C. Wong, Chem. Sci., 2018, 9, 6685
    DOI: 10.1039/C8SC01743C

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