24. A Silyl Ether-Protected Building Block for O-GlcNAcylated Peptide Synthesis to Enable One-Pot Acidic Deprotection

Abstract:

In this report, we introduce a novel building block for Fmoc/tBu solid phase peptide synthesis (SPPS) of β-linked O-GlcNAcylated peptides. This building block carries acid labile silyl ether protecting groups, which are fully removed under TFA-mediated peptide cleavage conditions from the resin, thus requiring fewer synthetic steps and no intermediate purification as compared to other acid or base labile protecting group strategies.

Yan, B.#; Li, W.#; Hackenberger, C.*, (2021) A silyl ether-protected building block for O-GlcNAcylated peptide synthesis to enable one-pot acidic deprotection, Org. Biomol. Chem.,19, 8014-8017, DOI: 10.1039/D1OB00510C (co-first author)