Amine capture strategy for peptide bond formation by means of quinolinium thioester salts |
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Authors: | Leleu Stéphane Penhoat Maël Bouet Alexis Dupas Georges Papamicaël Cyril Marsais Francis Levacher Vincent |
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Institution: | Laboratoire de Chimie Organique Fine et Hétérocyclique UMR 6014 IRCOF, CNRS, Université et INSA de Rouen, B.P 08, F-76131 Mont-Saint-Aignan Cédex, France. |
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Abstract: | A new and unprecedented exploitation of quinolinium thioester salts 2 in peptide bond formation is reported. These synthetic tools were assessed during the preparation of a number of dipeptides 3a-f obtained in good yields with complete stereochemical integrity. A sequential mechanism related to a prior amine capture strategy is well-established. Additionally, a tripeptide 3g was prepared according to a "safety-catch" approach, thus demonstrating the important potential of these new synthetic tools in the design of new safety-catch linkers exploitable in Solid-Phase Peptide Synthesis (SPPS). |
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