The dark side of disulfide-based dynamic combinatorial chemistry

Benjamin Ourri , Laurent Vial (1) , Mélissa Dumartin , Jean Septavaux , Marion Donnier-Maréchal , Emeric Jeamet , Elise Dumont , Florent Perret , Julien Leclaire

1 CNRS - Centre National de la Recherche Scientifique

During the last two decades, disulfide-based dynamic combinatorial chemistry has been extensively used in the field of molecular recognition to deliver artificial receptors for molecules of biological interest. Commonly, the nature of library members and their relative amounts are provided from HPLC-MS analysis of the libraries, allowing the identification of potential binders for a target (bio)molecule. By reinvestigating dynamic combinatorial libraries generated from a simple 2,5-dicarboxy-1,4-dithiophenol building block in water, we herein demonstrated that multiple analytical tools were actually necessary in order to comprehensively describe the libraries in terms of size, stereochemistry, affinity, selectivity, and finally to get a true grasp on the different phenomena at work within dynamic combinatorial systems.

Domaines: Chimie

Benjamin Ourri, Laurent Vial, Mélissa Dumartin, Jean Septavaux, Marion Donnier-Maréchal, et al.. The dark side of disulfide-based dynamic combinatorial chemistry. Chemical Science, 2020, 11 (31), pp.8151-8156. ⟨10.1039/D0SC02399J⟩. ⟨hal-02995793⟩