The glycosylation of proteins, specifically installation of O-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, C-GlcNAc Ser, has been prepared from the C-Glc Ser by a double inversion strategy using azide to insert the C-2 nitrogen functionality. The C-Glc Ser was available by a ring-closing metathesis and hydroalkoxylation route.
The glycosylation of proteins, specifically installation of O-GlcNAc on n class="Chemical">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, C-GlcNAcSer, has been prepared from the C-GlcSer by a double inversion strategy using azide to insert the C-2nitrogen functionality. The C-GlcSer was available by a ring-closing metathesis and hydroalkoxylation route.
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