Peptide Bond Formation via Nα-Protected Diacyldiselenides

Abstract

A simple, straightforward, for the peptide bond formation employing corresponding carboxylic acids and amines derived from amino acids via N α -protected diacyldiselenide is delineated. The key step of the synthesis is the in situ generation of N α -protected diacyldiselenide using NaBH 2 Se 3 as selenating reagent, followed by trapping with an amino acid ester leading to the peptide. The formation of N α -protected diacyldiselenide was confirmed through TLC and HRMS analysis using crude sample. The reaction is clean and all the products were obtained in moderate to good yields, including for sterically hindered amino acids. The protocol is free from racemisation, compatible with Fmoc, Cbz and Boc groups.