Dye-sensitized Photooxygenation of Tyrptophan: 3a-Hydroperoxypyrroloindole as a Labile Precursor of Formylkynurenine

Abstract

The isolation, structure determination, and reactivity of the tricyclic labile hydroperoxides 10 and 2 obtained by dye-sensitized photooxygenation of l-, d-, and dl-tryptophan and Nb-methoxycarbonyltryptophan ester are reported. The tricyclic hydroperoxide 10, under appropriate conditions, was easily convertible to formylkynurenine. Plausible mechanisms for these transformations are discussed. © 1981, The Pharmaceutical Society of Japan. All rights reserved.