Sugar-assisted glycopeptide ligation.
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.
Brik
Ashraf
A
Department of Chemistry and Skaggs Institute for Chemical Biology, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Yang
Yu-Ying
YY
Ficht
Simon
S
Wong
Chi-Huey
CH
D002241:Carbohydrates / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D006020:Glycopeptides / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D002241:Carbohydrates; D006020:Glycopeptides