Issue 14, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
18 Dec 2017
Accepted
05 Feb 2018
First published
05 Feb 2018

Org. Biomol. Chem., 2018,16, 2411-2420

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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