Model Reactions for the Biosynthesis of Thyroxine. XIX. The Formation of a Thyroxine Precursor by Photooxidation of 4-Hydroxy-3,5-diiodophenylpyruvic Acid in Organic Solvents

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概要

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• Photooxidation of 4-hydroxy-3,5-diiodophenylpyruvic acid (I) in methanol was found to yield a hydroperoxide (IV). This hydroperoxide reacted anaerobically with 3,5-diiodotyrosine (II) to form thyroxine (III). A photo-product, presumably IV, apparently accelerated the oxidation of I. Methanol, among several organic solvents, was found to be the best solvent for the photooxidation. Similar oxidations with 4-hydroxy-3-iodo-5-methoxyphenylpyruvic acid (V) and 4-hydroxyphenylpyruvic acid (VI) showed that the rate of oxidation decreased in the order I>V>VI. A product of the photooxidation of I, probably the hydroperoxide IV, also acts as an accelerator in the photooxidation of the desiodo analog VI of I.

• 公益社団法人 日本化学会の論文

著者

• Omura Kanji

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

関連論文

• Model Reactions for the Biosynthesis of Thyroxine. XIX. The Formation of a Thyroxine Precursor by Photooxidation of 4-Hydroxy-3,5-diiodophenylpyruvic Acid in Organic Solvents

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