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Paper | Special issue | Vol 47, No. 2, 1998, pp.865-870
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)93
Photooxidative Decarboxylation of Proline, a Novel Oxidative Stress to Natural Amines

Katsuya Endo,* Kaoru Hirayama, Yuko Aota, Kazuhiko Seya, Hirotatsu Asakura, and Kanehiko Hisamichi

*Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan

Abstract

Proline was decarboxylated quantitatively to Δ1-pyrroline on photoirradiation in the presence of rose bengal, while its methyl ester yielded an equimolar mixture of Δ1- and Δ5-pyrroline-2-carboxylic acid methyl esters. The decarboxylation of proline took place under either an aerobic ( O2 bubbling ) or an anaerobic ( N2 bubbling) conditions, and under the latter condition, extent of the reaction depended on the amount of rose bengal employed. These results imply mechanistically that the reaction is the Type I photooxidation, indicating a new type of oxidative stress to natural secondary amines.