Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Dye-sensitized Photooxygenation of Tyrptophan : 3a-Hydroperoxypyrroloindole as a Labile Precursor of Formylkynurenine
MASAKO NAKAGAWASHIRO KATOSHIGEHIRO KATAOKASHINICHI KODATOHIDEYUKI WATANABEHARUO OKAJIMATOHRU HINOBERNHARD WITKOP
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1981 Volume 29 Issue 4 Pages 1013-1026

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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.

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© The Pharmaceutical Society of Japan
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