Biomimetic Catalysis of Diketopiperazine and Dipeptide Syntheses

Abstract

Modular supramolecular catalysts with a coiled-coil peptide scaffold, designed to mimic nonribosomal peptide synthetases, catalyze the formation of diketopiperazines and linear dipeptides for several aminoacyl substrates (see scheme). The nature of the active-site residues in the peptide catalysts can be used to effect directed intermodular aminoacyl transfer processes and govern the relative yields of diketopiperazine, linear dipeptide, and hydrolyzed substrate. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z704266_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.