Regiospecific attack of nitrogen and sulfur nucleophiles on quinones derived from poison oak/ivy catechols (urushiols) and analogs as models for urushiol-protein …

…, VS Byers, RG Dennick, N Castagnoli Jr

Index: Liberato; Byers; Dennick; Castagnoli Jr. Journal of Medicinal Chemistry, 1981 , vol. 24, # 1 p. 28 - 33

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Citation Number: 70

Abstract

Attempts to characterize potential biologically important covalent interactions between electrophilic quinones derived from catechols present in poison &/ivy (urushiol) and biomacromolecules have led to the analysis of model reactions involving sulfur and amino nucleophiles with 3-heptadecylbenzoquinone. Characterization of the reaction products indicates that this quinone undergoes regiospecific attack by (S)-N-acetylcysteine at C-6 ...