Issue 23, 2014
From the journal:

Chemical Communications

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

Damien Beaufils,a   Grégoire Danger,b   Laurent Boiteau,a   Jean-Christophe Rossia  and  Robert Pascal*a  

* Corresponding authors

a Institut des Biomolécules Max Mousseron, UMR 5247, CNRS—Université Montpellier 1 & Montpellier 2, CC17006, Place E. Bataillon, 34095 Montpellier, France
E-mail: rpascal@univ-montp2.fr

b Spectrométries et Dynamique Moléculaire, Physique des Interactions Ioniques et Moléculaires, UMR 7345, CNRS—Aix-Marseille Université, Centre Saint-Jérôme—case 252, 13397 Marseille, Cedex 20, France

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

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Article information

DOI
https://doi.org/10.1039/C3CC49580A
Article type
Communication
Submitted
18 Dec 2013
Accepted
28 Jan 2014
First published
28 Jan 2014

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

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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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