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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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cris.lastimport.scopus2024-02-12T20:33:29Z
dc.abstract.enIn 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.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorUlatowski, Filip
dc.contributor.authorCholewiak, Agnieszka
dc.contributor.authorDobrzycki, Łukasz
dc.contributor.authorJurczak, Janusz
dc.date.accessioned2024-01-24T22:07:58Z
dc.date.available2024-01-24T22:07:58Z
dc.date.issued2018
dc.description.financeNie dotyczy
dc.description.number14
dc.description.volume16
dc.identifier.doi10.1039/C7OB03123H
dc.identifier.issn1477-0520
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/105051
dc.identifier.weblinkhttp://pubs.rsc.org/en/Content/ArticleLanding/2018/OB/C7OB03123H
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofOrganic and Biomolecular Chemistry
dc.relation.pages2411-2420
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.titleDisulphide bond exchange inhibited by air – kinetic and thermodynamic products in a library of macrocyclic cysteine derivatives
dc.typeJournalArticle
dspace.entity.typePublication