Abstract
Abstract Base-assisted electrophilic cleavage of sulfenate esters was studied with reference to possible biological models. It is suggested that sulfenate esters (RSOR') may serve as intermediates in oxidations involving alcohol dehydrogenases. Models for the biological oxidation of alcohols via sulfenate ester intermediates are presented. The lipoic acid catalyzed dehydrogenation step in the actions of α-ketoacid oxidases (e.g., pyruvic acid dehydrogenase and α-keto glutarate dehydrogenase) is also explained in terms of a possible sulfenate ester intermediate. In the interaction of alcohols and amines, with membrane proteins, the possibility of reversible formation of sulfenate esters and of sulfenamide formation is suggested. Experimental support is given for the formation of carbonyl compounds, from alcohols via sulfenate esters and subsequent electrophilic attack by N-iodosuccinimide on the esters. Such reactions of sulfenyl esters open virtually unexplored areas of chemistry and of the related biological implications. Methyl fluorosulfate (‘magic methyl’) in presence of base is also effective for the cleavage reaction.
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