Sugars are believed to play an important role in the signaling pathways of cells in diseased states such as diabetes. Of particular interest is the role O-GlcNAcylation plays in the regulation of the transcription factor FOXO1 which is known to be tightly controlled by insulin signaling. While it is known that O-GlcNAcylation triggers the increased transcription of gluconeogenic genes contributing to glucose toxicity in diabetic systems the means by which this post-translational modification is detected is not yet established. We seek to understand how FOXO1 O-GlcNAcylation can be altered to influence metabolic regulation through the use of labeled glycopeptide mimics. We further seek to determine the reader of this modification through the use of photoreactive glycopeptide mimics. Utilizing solid phase peptide synthesis, we can introduce chemically relevant moieties such as a diazirine, biotin, and/or fluorophore onto a peptide mimic of FOXO1. By introducing a non-labile sugar, the peptide mimic will be able to model the known O-GlcNAcylation sites of FOXO1. Ultimately our glycopeptide mimics will allow for investigation into the role O-GlcNAc signaling plays in metabolic diseases.

Glycopeptides mimetics as inhibitors of insulin resistance in a diabetes cell model

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.