Issue 23, 2014

Diastereoselectivity in prebiotically relevant 5(4H)-oxazolone-mediated peptide couplings

Abstract

A stereochemical study of a potentially prebiotic peptide-forming reaction was carried out as the first part of a systems chemistry investigation of potential paths for symmetry breaking. Substantial diastereomeric excesses result from a fast epimerization of the 5(4H)-oxazolone intermediate in aqueous solution.

Graphical abstract: Diastereoselectivity in prebiotically relevant 5(4H)-oxazolone-mediated peptide couplings

Supplementary files

Article information

Article type
Communication
Submitted
18 Dec 2013
Accepted
28 Jan 2014
First published
28 Jan 2014

Chem. Commun., 2014,50, 3100-3102

Diastereoselectivity in prebiotically relevant 5(4H)-oxazolone-mediated peptide couplings

D. Beaufils, G. Danger, L. Boiteau, J. Rossi and R. Pascal, Chem. Commun., 2014, 50, 3100 DOI: 10.1039/C3CC49580A

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