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• W2083428393 endingPage "662" @default.
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• W2083428393 abstract "The APED model (activation-polymerization-epimerization-depolymerization) is a unique example of a chemical system that allows symmetry breaking through a dynamic process involving indirect network autocatalysis. In its simplest version, the autocatalytic behavior of this model partly relies on the reproduction of local chiral centers in dipeptides through an epimerization process, with a thermodynamic preference for homochiral chains. We studied the reactivity of di- and tripeptides, containing a N-terminal phenylglycine (Phg) residue, as model compounds for the experimental determination of the kinetic and thermodynamic parameters related to the N-terminal epimerization process. Although the N-terminal residue is prone to spontaneous epimerization, catalysis was required for the epimerization to reach the equilibrium state in reasonable time. Unexpectedly, the observed equilibrium diastereoisomeric excesses have shown a general tendency for more stable heterochiral peptides, especially strong in the case of dipeptides. In parallel to this process, a stereoselective peptide cleavage through diketopiperazine formation was observed. Contrary to the N-terminal epimerization of peptides, the diketopiperazine formation did not need any catalyst, and heterochiral peptides were shown to be dynamically unstabilized, as they were cleaved faster than homochiral peptides. The validity of the extrapolation of these results to other residues and longer peptide chains is discussed, and some directions for future developments of the theoretical model are given." @default.
• W2083428393 created "2016-06-24" @default.
• W2083428393 creator A5034479918 @default.
• W2083428393 creator A5075386261 @default.
• W2083428393 creator A5080336333 @default.
• W2083428393 date "2010-08-01" @default.
• W2083428393 modified "2023-09-25" @default.
• W2083428393 title "An Experimental Investigation of the Evolution of Chirality in a Potential Dynamic Peptide System: <i>N</i>-Terminal Epimerization and Degradation into Diketopiperazine" @default.
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• W2083428393 doi "https://doi.org/10.1089/ast.2009.0450" @default.
• W2083428393 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/20735255" @default.
• W2083428393 hasPublicationYear "2010" @default.
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