For the synthesis of proteoglycan glycopeptide, the incorporation of multiple aspartic acids in core peptide and O- and N-sulfated glycan chain remains challenging. A sulfate ester strategy is described here using dichlorovinyl (DCV) group as the protective group for the synthesis of syndecan-4 glycopeptide. Upon acidic cleavage of side chain protecting groups in core peptide, DCV groups can be removed to released free O-, N-sulfation and multiple aspartic acids containing glycopeptide, which is prepared for the first time. The binding synthetic compounds to protein fibroblast growth factor 2 (FGF-2), chemokines IL8 and CCL13 reveal both glycan chain and core peptide play the role in protein binding.

Chemical synthesis of syndecan-4 glycopeptide bearing O-, N-sulfation, and aspartic acids utilizing sulfate ester strategy

2019 Fall National Meeting

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