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■ Chemical Behavior of Isolated Thiamin Ylide in Neutral Aqueous Solutiion — A New Mechanism of Interconversion of Thiamin and Thiamin Thiolate

Hirihiko Sugimoto and Kentaro Hirai

*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan

Abstract

The isolated thiamin ylide (TY) was found to he converted into thiamin thiolate (TH⁺TS^-, 3) in neutral aqueous solution. The formation of the ion-pair can best be explained by the disproportionation of the ylide into the yellow form (TH⁺YF^-, 4) followed by ring-opening by the attack of water to pyrimido[4,5-d]pyrimidine ring of the yellow form. These results suggested a new mechanism for the interconversion between thiamin (TH⁺CI^-) and thiamin thiolate (Na⁺TS^-).