title: Synthesis of dipeptide 4-nitroanilides containing non-proteinogenic amino acids.
abstract: A series of tert-butyloxycarbonyl amino acid 4-nitroanilides, including N-alkylated amino acids and (R)-thiazolidine-4-carboxylic acid, (S)-oxazolidine-4-carboxylic acid. (4S,5S)-5-methyloxazolidine-4-carboxylic acid, (4S,5R)-5-methyloxazolidine-4-carboxylic acid, (S)-azetidine-2-carboxylic acid, (S)-pipecolic acid and (S)-3,4-dehydroproline, were prepared conveniently by the isocyanate method or the mixed anhydride procedure. The resulting amino acid 4-nitroanilides were extended to corresponding dipeptide 4-nitroanilides with tert-butyloxycarbonyl-(S)-alanine. In the case of sterically hindered amino acid 4-nitroanilides the mixed anhydride procedure with diphenylphosphinyl chloride was successful.
authors.affiliation: Max Planck Institute for the Advancement of Science, Halle, Germany.
authors.forename: M
authors.initials: M
authors.lastname: Schutkowski
authors.forename: C
authors.initials: C
authors.lastname: Mrestani-Klaus
authors.forename: K
authors.initials: K
authors.lastname: Neubert
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D000813:Anilides / Q000138:chemical synthesis*; D010455:Peptides / Q000138:chemical synthesis*
chemical_list: D000596:Amino Acids; D000813:Anilides; D010455:Peptides