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Issue 14, 2018
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Disulphide bond exchange inhibited by air – kinetic and thermodynamic products in a library of macrocyclic cysteine derivatives

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Abstract

In this paper we present the synthesis and reactivity of dithiols comprising of two cysteine moieties attached to a dipicolinic acid core. Oxidation of these thiols provides oligomeric macrocycles. Monomers with 13-membered rings are kinetic products which are, however, strained and readily transform into higher oligomers under basic conditions or elevated temperature via a disulphide exchange reaction. Dimers, which are the most stable thermodynamic products, equilibrate only under inert conditions with thiolate as a catalyst. Under aerobic conditions, the thiols are oxidised before the equilibrium is reached.

Graphical abstract: Disulphide bond exchange inhibited by air – kinetic and thermodynamic products in a library of macrocyclic cysteine derivatives

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Publication details

The article was received on 18 Dec 2017, accepted on 05 Feb 2018 and first published on 05 Feb 2018


Article type: Paper
DOI: 10.1039/C7OB03123H
Citation: Org. Biomol. Chem., 2018,16, 2411-2420
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    Disulphide bond exchange inhibited by air – kinetic and thermodynamic products in a library of macrocyclic cysteine derivatives

    A. Cholewiak, Ł. Dobrzycki, J. Jurczak and F. Ulatowski, Org. Biomol. Chem., 2018, 16, 2411
    DOI: 10.1039/C7OB03123H

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