Rapid formation of N-Glycopeptides via Cu(II)-promoted glycosylative ligation.
Herein is described the chemoselective Cu(II)-HOBt promoted chemical ligation of glycosylamines and peptide thioacids to give N-glycosylated peptides. The method is distinguished from other chemical approaches to peptide N-glycosylation in that (1) it can be employed in the presence of unprotected N-terminal and Lys side chain amines; (2) it is remarkably fast, going to completion in under 30 min; and (3) it produces glycopeptides without attendant aspartimide formation.
Department of Chemistry, Washington State University, Pullman, Washington 99164-4630, United States.
Ryan
R
Joseph
Frank Brock
FB
Dyer
Philip
P
Garner
D000595:Amino Acid Sequence; D001224:Aspartic Acid / Q000031:analogs & derivatives / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D008239:Lysine / Q000737:chemistry; D015394:Molecular Structure
D006020:Glycopeptides; D001224:Aspartic Acid; C075871:aspartimide; D003300:Copper; D008239:Lysine