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Literature DB >> 24513651

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

Damien Beaufils¹, Grégoire Danger, Laurent Boiteau, Jean-Christophe Rossi, Robert Pascal.

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.

Entities: Chemical

Mesh：

Substances：
Peptides
Oxazolone

Year: 2014 PMID： 24513651 DOI： 10.1039/c3cc49580a

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

6 in total

1. The Activation of Free Dipeptides Promoted by Strong Activating Agents in Water Does not Yield Diketopiperazines.

Authors: Damien Beaufils; Sandra Jepaul; Ziwei Liu; Laurent Boiteau; Robert Pascal
Journal: Orig Life Evol Biosph Date: 2015-07-24 Impact factor: 1.950

2. Templates direct the sequence-specific anchoring of the C-terminus of peptido RNAs.

Authors: Biswarup Jash; Clemens Richert
Journal: Chem Sci Date: 2020-03-02 Impact factor: 9.825

3. Evolutionary importance of the intramolecular pathways of hydrolysis of phosphate ester mixed anhydrides with amino acids and peptides.

Authors: Ziwei Liu; Damien Beaufils; Jean-Christophe Rossi; Robert Pascal
Journal: Sci Rep Date: 2014-12-11 Impact factor: 4.379

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

1. The Activation of Free Dipeptides Promoted by Strong Activating Agents in Water Does not Yield Diketopiperazines.

2. Templates direct the sequence-specific anchoring of the C-terminus of peptido RNAs.

3. Evolutionary importance of the intramolecular pathways of hydrolysis of phosphate ester mixed anhydrides with amino acids and peptides.

4. Mixed Anhydride Intermediates in the Reaction of 5(4H)-Oxazolones with Phosphate Esters and Nucleotides.

5. Synthesis of a Peptidoyl RNA Hairpin via a Combination of Solid-Phase and Template-Directed Chain Assembly.

6. Fatty acids' double role in the prebiotic formation of a hydrophobic dipeptide.