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Synthèse d'analogues de l'épicocconone par réaction d'oxydation désaromatisante : relation structure fluorescences et application en protéomique

Abstract : Epicocconone is a tricyclic natural product of azaphilone family, isolated from the fungus Epicoccum nigrum. This compound covalently binds to primary amines, leading to a protein linked conjugate which is strongly fluorescent. This reaction, reversible according to the pH, makes of this compound an excellent proteins dye compatible with an analysis by mass spectrometry. Synthesis of epicocconone’s analogues has been undertaken in our laboratory.This synthesis is based on a key oxidative dearomatization. A study of this reaction allowed us to shed light on a high diastereoselectivity according to reaction conditions. After introduction of functionalized acylfuranone ring, a library of epicocconone’s analogues was obtained allowing us to establish the structure-fluorescence relationship and to estimate the use of these biomarkers in proteomics.
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Submitted on : Thursday, September 27, 2012 - 10:17:19 AM
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Agathe Boulangé. Synthèse d'analogues de l'épicocconone par réaction d'oxydation désaromatisante : relation structure fluorescences et application en protéomique. Chimie organique. INSA de Rouen, 2012. Français. ⟨NNT : 2012ISAM0002⟩. ⟨tel-00735882⟩

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