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

Abstract

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.

Keywords:

• acylation
• 5‐amino‐1‐methyl‐1H‐[1,2,4]triazole‐3‐carboxylic acid
• benzotriazolide
• FTIR spectra
• hetareneamino acid
• NMR spectra
• peptide synthesis

Acknowledgments

The authors gratefully acknowledge the University of Opole for grant number 1/S/2005.