Design of an Organocatalyst for Peptide Synthesis

Key words

organocatalysis - urea-based catalysis - diselenides - selenoesters - peptide coupling

Significance

Because to the growing impact of peptides as biological reagents and therapeutics, the development of efficient methods for the construction of amide bonds is an important research area for organic chemists. The authors have designed an organocatalyst based on the concept of urea-based hydrogen bonding and covalent catalysis for amide bond formation.

Comment

The designed diselenide catalyst activates the carboxylic acid as a selenoester by a reduction–oxidation condensation procedure. The developed macrocyclic diselenide catalyst showed near-quantitative conversion, was active for a diverse range of amino acids without significant racemization, and was reactive in solid-phase peptide synthesis.Further insights can also be found in this issue: Synfacts 2019, 15, 1424.