Synthesis of β-C-GlcNAc Ser from β-C-Glc Ser
Ernest G Nolen1, Leyan Li, Kristopher V Waynant
1Department of Chemistry, Colgate University, Hamilton, New York 13346, USA. enolen@colgate.edu
Abstract:
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.
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