Site-specific modification of amino acids and peptides by aldehyde-alkyne-amine coupling under ambient aqueous conditions.
A highly efficient method for the direct, site-specific functionalization of amino acids and peptides, under ambient conditions, is described. In aqueous, nearly solvent-free conditions, copper(I) chloride catalyzed the aldehyde-alkyne-amine (A(3)) coupling of amino acids to form dipropargylated products in moderate to excellent yields. The propargylamine functionality provides a convenient handle for further structural modifications, demonstrated by a subsequent one-pot deprotection and "click" reaction and a solution-phase peptide coupling.
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A0B8, Canada. nicholas.uhlig@mail.mcgill.ca
Nick
N
Uhlig
Chao-Jun
CJ
Li
D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D000447:Aldehydes; D000480:Alkynes; D000588:Amines; D000596:Amino Acids; D010455:Peptides; D014867:Water