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• W2801169841 abstract "O-GlcNAc transferase (OGT) is an essential glycosyltransferase that installs the O-GlcNAc post-translational modification on the nucleocytoplasmic proteome. We report the development of S-linked UDP-peptide conjugates as potent bisubstrate OGT inhibitors. These compounds were assembled in a modular fashion by photoinitiated thiol-ene conjugation of allyl-UDP and optimal acceptor peptides in which the acceptor serine was replaced with cysteine. The conjugate VTPVC(S-propyl-UDP)TA ( Ki = 1.3 μM) inhibits the OGT activity in HeLa cell lysates. Linear fusions of this conjugate with cell penetrating peptides were explored as prototypes of cell-penetrant OGT inhibitors. A crystal structure of human OGT with the inhibitor revealed mimicry of the interactions seen in the pseudo-Michaelis complex. Furthermore, a fluorophore-tagged derivative of the inhibitor works as a high affinity probe in a fluorescence polarimetry hOGT assay." @default.
• W2801169841 created "2018-05-17" @default.
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• W2801169841 date "2018-05-03" @default.
• W2801169841 modified "2023-10-09" @default.
• W2801169841 title "Thio-Linked UDP–Peptide Conjugates as O-GlcNAc Transferase Inhibitors" @default.
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• W2801169841 doi "https://doi.org/10.1021/acs.bioconjchem.8b00194" @default.
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