title: Synthesis of β-C-GlcNAc Ser from β-C-Glc Ser.
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.
authors.affiliation: Department of Chemistry, Colgate University, Hamilton, New York 13346, USA. enolen@colgate.edu
authors.forename: Ernest G
authors.initials: EG
authors.lastname: Nolen
authors.forename: Leyan
authors.initials: L
authors.lastname: Li
authors.forename: Kristopher V
authors.initials: KV
authors.lastname: Waynant
mesh_terms: D000117:Acetylglucosamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D012694:Serine / Q000031:analogs & derivatives / Q000737:chemistry*
chemical_list: D012694:Serine; D000117:Acetylglucosamine