The dark side of disulfide-based dynamic combinatorial chemistry.

Chemical Science
Mélissa DumartinJulien Leclaire

Abstract

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 re-investigating 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.

References

Aug 3, 2006·Journal of the American Chemical Society·Laurent VialSijbren Otto
Sep 14, 2006·Chemical Reviews·Peter T CorbettSijbren Otto
Aug 22, 2008·Journal of the American Chemical Society·R Frederick Ludlow, Sijbren Otto
Dec 5, 2009·The Journal of Organic Chemistry·A Gastón Orrillo, Ricardo L E Furlan
Oct 17, 2012·Organic Letters·Saleh HamiehSijbren Otto
Oct 12, 2013·Angewandte Chemie·Saleh HamiehSijbren Otto
Jul 21, 2015·Journal of the American Chemical Society·Piotr NowakJianwei Li
Dec 23, 2015·The Journal of Organic Chemistry·Pierre-Thomas SkowronJulien Leclaire
Nov 23, 2016·Chemical Communications : Chem Comm·Laurent VialJulien Leclaire
Feb 13, 2019·Chemical Science·Emeric JeametJulien Leclaire

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Citations

Jun 5, 2021·Angewandte Chemie·Tanausú SantosRomen Carrillo

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Methods Mentioned

BETA
NMR

Software Mentioned

lsqcurvefit
Amber
fsolve
MATLAB

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