Aza-1,2,3-triazole-3-alanine synthesis via copper-catalyzed 1,3-dipolar cycloaddition on aza-progargylglycine.
The parallel synthesis of seven aza-1,2,3-triazole-3-alanine azapeptides of the Growth Hormone Releasing Peptide-6 (GHRP-6) was accomplished via a Cu-catalyzed azide-alkyne [3+2] cycloaddition on an aza-propargylglycine residue anchored on Rink amide resin. Circular dichroism spectroscopy in water demonstrated that azapeptides which possess an aza-1,2,3-triazole-3-alanine residue at the Trp(4) position of the GHRP-6 sequence adopt beta-turn conformations.
Proulx
Caroline
C
Département de Chimie, Université de Montréal, C.P. 6128, Succursale Centre-Ville, Montréal, Québec H3C 3J7, Canada.
Lubell
William D
WD
D000409:Alanine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D000480:Alkynes / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D013058:Mass Spectrometry
D000480:Alkynes; D001372:Aza Compounds; C009055:propargylglycine; D003300:Copper; D000409:Alanine; D005998:Glycine