Heparins are highly sulfated glycosaminoglycan polysaccharides that exhibit anticoagulant activity. The commercial drug, fondaparinux sodium, is a structurally homogeneous heparin pentasaccharide (an ultralow molecular weight heparin). It's current chemical synthesis is rather lengthy and low yielding. A promising alternative approach developed by our laboratory and others is to chemoenzymatically synthesize heparins, utilizing a commercially available monosaccharide acceptor and uridine diphosphate (UDP) sugar donors. Fondaparinux synthesis requires a heparosan backbone structure of defined size that can be specifically N-sulfonated and selectively modified by the heparan sulfate (HS) sulfotransferases and C5-epimerase. This presentation describes efforts to scale the synthesis of heparosan oligosaccharides, key intermediates in the chemoenzymatic synthesis of Arixtra.

Chemoenzymatic synthesis of heparosan oligosaccharides

245th National Meeting (2013)

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