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Participation of an Intermediate Sulfoxide in the Enzymatic Thiolation of the Imidazole Ring of Hercynine to Form Ergothioneine

From the ¹ From the Department of Biochemistry, University of Vermont College of Medicine, Burlington, Vermont 05401

Cell-free extracts of Neurospora crassa have been obtained which in the presence of O₂ and Fe²⁺ catalyze the transfer of the sulfur atom of cysteine to the imidazole ring of hercynine (histidine betaine) to form ergothioneine (2-mercaptohistidine betaine). The general nature of the conversion has been established by the isolation of an intermediate compound, S-(ß-amino-ß-carboxyethyl)ergothioneine sulfoxide, which is subsequently converted by a pyridoxal-requiring enzyme to ergothioneine and pyruvate. Chemical synthesis of the intermediate sulfoxide has been accomplished by the condensation of ß-chloroalanine with ergothioneine and oxidation of the resultant thioether with hydrogen peroxide.

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