Proteoglycans are a family of complex glycoproteins with glycosaminoglycan (GAG) chains such as heparan sulfate (HS) and chondroitin sulfate (CS) attached to the core protein backbone. Due to the high structural heterogeneity of GAG in nature, it is challenging to decipher the respective roles of the glycan chain and the core protein on proteoglycan functions. While the sulfation patterns of GAGs dictate many activities, the core protein can potentially impact their functions as well. In order to decipher this, homogeneous proteoglycan glycopeptides are needed. In this presentation, we will present our efforts toward the first successful synthesis of proteoglycan glycopeptides bearing multiple aspartic acids in the core peptide and <i>O</i>- and <i>N</i>-sulfations in the glycan chain, as exemplified by the syndecan-4 glycopeptides. In addition, efforts integrating chemical and enzymatic methods to greatly enhance the overall synthetic efficiency will be discussed.

Synthesis of proteoglycan glycopeptides

ACS Fall 2020 Virtual Meeting

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