Heparan sulfate (HS) is a glycosaminoglycan that is abundantly present on cell surfaces and in the extracellular matrix in animal tissues. HS binds with various proteins and is essential for regulating their activities during wound healing, inflammation, angiogenesis, and is also exploited by several bacterial and viral pathogens. The biosynthesis of HS is heterogeneous and produces a complex mixture of sulfated epitopes that has limited progress in identifying biologically active structures. For this reason, we are developing a diversity-oriented approach toward the synthesis of well-defined HS derivatives, one which sets the stereochemical configuration of the uronic acid (L-IdoA versus D-GlcA) at a late stage. This approach involves an orthogonally protected 4-deoxypentenoside (4-DP) disaccharide as a key intermediate, which can be stereoselectively epoxidized and converted by stereoselective ring opening into a terminal D- or L-hexopyranoside.

Synthesis of heparin-like compounds using a diversity-oriented approach

246th National Meeting (2013)

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