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Synthetic Studies Of Heparan Derivatives: Glycosyl Couplings And Post-Glycosylative Modifications, Hari Raj Khatri

Open Access Dissertations

Heparan sulfate (HS) and closely related heparin are comprised of alternating units of D-glucosamine and either D-glucuronic acid (D-GluA) or L-iduronic acid (L-IdoA), and support variable degrees of sulfation which can interact with a large number of proteins with diverse biological functions. HS oligosaccharides can be constructed from readily accessible D-GlcN and D-GlcA derivatives, but the inclusion of L-IdoA is less straightforward. To address this, our laboratory has developed alternative synthetic strategies for HS-like oligosaccharides to incorporate either D-GlcA or L-IdoA in a synthetically efficient manner by nucleophilic ring opening of 4-epoxypyranosides, which can be made from readily available D-hexoses …