title: Diversity-oriented synthesis of azapeptides with basic amino acid residues: aza-lysine, aza-ornithine, and aza-arginine.
abstract: Aza-peptides with basic amino acid residues (lysine, ornithine, arginine) and derivatives were synthesized by an effective approach featuring alkylation of a hydrazone-protected aza-glycine residue with α-bromo ω-chloro propane and butane to provide the corresponding alkyl chloride side chains. Displacement of the chloride with azide and various amines gave entry to azaOrn, azaLys, and azaArg containing peptides as demonstrated by the solution and solid-phase syntheses of 29 examples, including an aza-library of Growth Hormone Releasing Peptide-6 analogs.
authors: Département de Chimie, Université de Montréal , C.P. 6128, Succursale Centre-Ville, Montréal, Québec, Canada H3C 3J7.
authors: Mariam
authors: M
authors: Traoré
authors: Ngoc-Duc
authors: ND
authors: Doan
authors: William D
authors: WD
authors: Lubell
mesh_terms: D024361:Amino Acids, Basic / Q000737:chemistry*; D001120:Arginine / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008239:Lysine / Q000737:chemistry*; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D009952:Ornithine / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques
chemical_list: D024361:Amino Acids, Basic; D001372:Aza Compounds; D009842:Oligopeptides; D010455:Peptides; C041048:growth hormone releasing hexapeptide; D001120:Arginine; D009952:Ornithine; D008239:Lysine