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

Damien Beaufils; Grégoire Danger; Laurent Boiteau; Jean-Christophe Rossi; Robert Pascal

doi:10.1039/c3cc49580a

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

Journal article

Peer reviewed

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

Damien Beaufils, Grégoire Danger, Laurent Boiteau, Jean-Christophe Rossi and Robert Pascal

Chemical Communications, Vol.50(23), pp.3100-3102

2014

DOI: https://doi.org/10.1039/c3cc49580a

Abstract

Diastereoselectivity, 5(4H)-oxazolone-mediated, peptide, couplings, prebiotic, aqueous solution

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.

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Title: Diastereoselectivity in prebiotically relevant 5(4H)-oxazolone-mediated peptide couplings
Creators - without role: Damien Beaufils - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Grégoire Danger - Aix-Marseille Université
Laurent Boiteau - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Jean-Christophe Rossi - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Robert Pascal - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Publication Details: Chemical Communications, Vol.50(23), pp.3100-3102
Identifiers: 9942724909311
Academic Unit: Institut des Biomolécules Max Mousseron - IBMM
Language: English
Resource Type: Journal article
Local Fields: hal-01930550