title: Efficient stereoselective synthesis of gamma-N-glycosyl asparagines by N-glycosylation of primary amide groups.
abstract: The efficient and elegant synthesis of N-glycosides by N-glycosylation of asparagine-containing peptides is described. Glycosylation of primary amides with glycosyl N-phenyltrifluoroimidates in the presence of a catalytic amount of TMSOTf in nitromethane smoothly proceeded to provide the corresponding N-glycosyl amino acids in excellent yields. This coupling method was adaptable to the coupling of various glycosyl donors with amino acids and peptides.
authors.affiliation: Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Tanaka
authors.forename: Yuki
authors.initials: Y
authors.lastname: Iwata
authors.forename: Daisuke
authors.initials: D
authors.lastname: Takahashi
authors.forename: Masaatsu
authors.initials: M
authors.lastname: Adachi
authors.forename: Takashi
authors.initials: T
authors.lastname: Takahashi
mesh_terms: D000081:Acetamides / Q000737:chemistry; D001216:Asparagine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D004151:Dipeptides / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D013237:Stereoisomerism
chemical_list: D000081:Acetamides; D004151:Dipeptides; D006020:Glycopeptides; D006027:Glycosides; D001216:Asparagine; C030686:acetamide