Peptide Synthesis with 5-Amino-1-methyl-1H-[1,2,4]triazole-3-carboxylic Acid

• Published in: Synthetic communications Vol. 37; no. 11; pp. 1917 - 1925
• Main Authors: Masiukiewicz, Elżbieta, Rzeszotarska, Barbara, Wawrzycka-Gorczyca, Irena, Kołodziejczyk, Edyta
• Format: Journal Article
• Language: English
• Published: Taylor & Francis Group 01-01-2007
• Subjects: 5-amino-1-methyl-1H-[1,2,4]triazole-3-carboxylic acid; acylation; benzotriazolide; FTIR spectra; hetareneamino acid; NMR spectra; peptide synthesis
• ISSN: 0039-7911; 1532-2432
• DOI: 10.1080/00397910701341423

In the search for the peptide synthesis of new potential lexitropsins, starting with methyl 5-amino-1-methyl-1H-[1,2,4]triazole-3-carboxylate 1a, we synthesized the chloroacetyl derivative of 2a, which was hydrolyzed to acid 2b and ammonolyzed to the peptide 2c. A more effective route was the use of (t-butoxycarbonyl)glycyl-benzotriazolide 3 to the acylation 1a, which leads the N/C protected peptide 4. This peptide was selectively N-deprotected to be the useful segment 5 for further peptide syntheses to the N-terminus. It was also C-deprotected, that is hydrolyzed to give peptide 2c for further C-extension. To the best of our knowledge, this is the first peptide that is a derivative of amino-1-methyl-1H-[1,2,4]triazole-carboxylic acid.