Synthesis of β‑<i>C</i>‑GlcNAc Ser from β‑<i>C</i>‑Glc Ser

Abstract

The glycosylation of proteins, specifically installation of <i>O</i>-GlcNAc on Ser/Thr residues, is a dynamic control element for transcription repression, protein degradation, and nutrient sensing. To provide homogeneous and stable structures with this motif, the synthesis of a C-linked mimic, <i>C</i>-GlcNAc Ser, has been prepared from the <i>C</i>-Glc Ser by a double inversion strategy using azide to insert the C-2 nitrogen functionality. The <i>C</i>-Glc Ser was available by a ring-closing metathesis and hydroalkoxylation route