Copper-catalyzed N-arylation of semicarbazones for the synthesis of aza-arylglycine-containing aza-peptides.
Parallel synthesis of 13 aza-arylglycine peptides, based on the hexapeptide sequence of Growth Hormone Releasing Peptide-6 (GHRP-6), was accomplished via selective N-arylation of a semicarbazone peptide building block anchored on Rink amide resin. Aza-peptides possessing aza-indolylglycine and aza-imidazoylglycine residues were obtained through use of the corresponding heteroaryl iodides, yielding, respectively, aza-Trp and aza-His peptidomimics. CD spectroscopy indicated the propensity for aza-peptides, containing aza-arylglycines at the Trp(4) position of the GHRP-6 sequence, to adopt beta-turns.
Departement de Chimie, Université de Montréal, C.P. 6128, Succursale Centre-Ville, Montréal, Québec H3C 3J7.
Caroline
C
Proulx
William D
WD
Lubell
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D008968:Molecular Conformation; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D012664:Semicarbazones / Q000737:chemistry*; D013237:Stereoisomerism
D001372:Aza Compounds; D007454:Iodides; D010455:Peptides; D012664:Semicarbazones; D003300:Copper; C073870:cuprous iodide; D005998:Glycine