title: Sugar-assisted glycopeptide ligation.
abstract: The chemical synthesis of glycopeptides and glycoproteins from readily available materials presents an attractive route to homogeneous products for structural and functional studies. Chemical synthesis of glycopeptides and glycoproteins based on native chemical ligation represents one of the useful methods for the synthesis of natural glycopeptide structures. Here we describe a method that allows for the synthesis of glycopeptides from cysteine-free peptides. This method utilizes a peptide thioester and a glycopeptide in which the sugar moiety is modified with a thiol handle at the C-2 position. Upon completion of the ligation reaction, the thiol handle can be reduced with H2/metal to the acetamide moiety, furnishing the unmodified glycopeptides. Together, this sequence of reactions displays an attractive potential in glycopeptides and glycoproteins synthesis.
authors.affiliation: Department of Chemistry and Skaggs Institute for Chemical Biology, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Ashraf
authors.initials: A
authors.lastname: Brik
authors.forename: Yu-Ying
authors.initials: YY
authors.lastname: Yang
authors.forename: Simon
authors.initials: S
authors.lastname: Ficht
authors.forename: Chi-Huey
authors.initials: CH
authors.lastname: Wong
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D006020:Glycopeptides / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D002241:Carbohydrates; D006020:Glycopeptides