Chemoenzymatic Synthesis of Ultra Low Molecular Weight Heparins

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Heparin, an anticoagulant, was first used in 1916 - one of the few drugs still in use which predates the establishment of the FDA. Heparin is a long, highly negatively charged polysaccharide known as a glycosaminoglycan, or GAG. While the naturally occurring polysaccharide is quite long, the anticoagulant properties of heparin are due to a short, five saccharide section of the molecule, found in only a third of the long heparin chain. A synthetic analog of this pentasaccharide sequence, Fondaparinux, can act as a substitute for natural heparin under certain conditions. Our lab, together with Dr. Liu of the University of North Carolina at Chapel Hill, has synthesized two analogs of Fondaparinux with anticoagulant activity using a chemoenzymatic approach.