title: Encouraging progress in the ω-aspartylation of complex oligosaccharides as a general route to β-N-linked glycopolypeptides.
abstract: Described herein is a method for the joining of complex peptides to complex oligosaccharides via an N-linkage. The ω-aspartylation is conducted by coupling fully deprotected glycosylamine with a peptide containing a unique thioacid at the ω-aspartate carboxyl. In the presence of HOBT, under conditions that, in principle, allow for oxidation, complex components are combined in encouraging yields to produce structurally and stereochemically defined N-linked glycopolypeptides wherein the carbohydrate domain can be quite complex. Various mechanisms for oxidative coupling are proposed.
authors.affiliation: Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10065, United States.
authors.forename: Ping
authors.initials: P
authors.lastname: Wang
authors.forename: Xuechen
authors.initials: X
authors.lastname: Li
authors.forename: Jianglong
authors.initials: J
authors.lastname: Zhu
authors.forename: Jin
authors.initials: J
authors.lastname: Chen
authors.forename: Yu
authors.initials: Y
authors.lastname: Yuan
authors.forename: Xiangyang
authors.initials: X
authors.lastname: Wu
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Danishefsky
mesh_terms: D000588:Amines / Q000737:chemistry; D000595:Amino Acid Sequence; D001224:Aspartic Acid / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D009844:Oligosaccharides / Q000737:chemistry*
chemical_list: D000588:Amines; D006020:Glycopeptides; D009844:Oligosaccharides; D001224:Aspartic Acid; D009584:Nitrogen