title: Synthesis of mimetic peptides containing glucosamine.
abstract: A convenient synthesis of 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-d-glucopyranoside was described from the readily available starting material 2-acetamido-2-deoxy-d-glucose (N-acetyl-d-glucosamine). Herein, the coupling of different lipophilic amino acids with 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-d-glucose was reported via an amide linkage as useful building blocks for the synthesis of glycopeptides. Of particular interest, bioactive peptide Arg-Gly-Asp (RGD) was incorporated into the building block containing valine was also reported. The 15 examples of corresponding di-, tri- and tetra-peptides were obtained as single αanomers.
authors.affiliation: College of Pharmaceutical Sciences, Capital Medical University, Beijing 100069, People's Republic of China. jwzhang2006@163.com
authors.forename: Jianwei
authors.initials: J
authors.lastname: Zhang
authors.forename: Ming
authors.initials: M
authors.lastname: Zhao
authors.forename: Shiqi
authors.initials: S
authors.lastname: Peng
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry; D000606:Amino Sugars / Q000737:chemistry; D005944:Glucosamine / Q000737:chemistry*; D015394:Molecular Structure; D009842:Oligopeptides / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000606:Amino Sugars; D009842:Oligopeptides; D010455:Peptides; C047981:arginyl-glycyl-aspartic acid; D005944:Glucosamine; D000117:Acetylglucosamine