title: Chemical synthesis of N-linked glycans carrying both mannose-6-phosphate and GlcNAc-mannose-6-phosphate motifs.
abstract: Mannose-6-phosphate (M6P) containing N-linked glycans are the essential targeting signals for hydrolases sorting in eukaryotic cells. To facilitate their structural and binding analyses, a highly efficient and convergent method has been developed to prepare complex N-linked glycans with well-defined M6P and N-acetylglucosamine (GlcNAc)-M6P motifs, a newly identified binding element for M6P receptors. The GlcNAc-M6P motif was stereoselectively installed at the late stage of the synthesis. Sequential deprotection of benzyl and acetate groups provided the fully deprotected N-glycans in excellent yield.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.
authors.forename: Yunpeng
authors.initials: Y
authors.lastname: Liu
authors.forename: Gong
authors.initials: G
authors.lastname: Chen
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry*; D006023:Glycoproteins / Q000737:chemistry; D006867:Hydrolases / Q000737:chemistry*; D008360:Mannosephosphates / Q000737:chemistry*; D015394:Molecular Structure; D009844:Oligosaccharides / Q000737:chemistry*; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D011485:Protein Binding; D013237:Stereoisomerism; D013403:Sugar Phosphates / Q000737:chemistry*
chemical_list: D006023:Glycoproteins; D008360:Mannosephosphates; D009844:Oligosaccharides; D011134:Polysaccharides; D013403:Sugar Phosphates; C027693:mannose-6-phosphate; D006867:Hydrolases; D000117:Acetylglucosamine