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Angew Chem Int Ed Engl. 2014 Sep 8;53(37):9876-9. doi: 10.1002/anie.201404154. Epub 2014 Jul 15.

Synthesis of the heparin-based anticoagulant drug fondaparinux.

Author information

1
Genomics Research Center, Academia Sinica, No. 128 Academia Road, Section 2, Taipei 115 (Taiwan); Department of Chemistry, National Tsing Hua University, No. 101, Section 2, Kuang-Fu Road, Hsinchu 300 (Taiwan).

Abstract

Fondaparinux, a synthetic pentasaccharide based on the heparin antithrombin-binding domain, is an approved clinical anticoagulant. Although it is a better and safer alternative to pharmaceutical heparins in many cases, its high cost, which results from the difficult and tedious synthesis, is a deterrent for its widespread use. The chemical synthesis of fondaparinux was achieved in an efficient and concise manner from commercially available D-glucosamine, diacetone α-D-glucose, and penta-O-acetyl-D-glucose. The method involves suitably functionalized building blocks that are readily accessible and employs shared intermediates and a series of one-pot reactions that considerably reduce the synthetic effort and improve the yield.

KEYWORDS:

anticoagulant; carbohydrates; heparin; one-pot reactions; total synthesis

PMID:
25044485
DOI:
10.1002/anie.201404154
[Indexed for MEDLINE]
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