Mechanism of dye-sensitized photooxidation of tryptophan, tryptamine, and their derivatives. Singlet oxygen process in competition with type I process.
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概要
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Photosensitized oxidations of tryptophan (Trp), tryptamine, and their derivatives were investigated with a variety of sensitizers. Rose Bengal sensitized photooxidations proceed exclusively <I>via</I> Type II mechanism (singlet oxygen mechanism), whereas for thionine-sensitized photooxidations both Type I (nonsinglet oxygen mechanisms) and Type II mechanisms are operative under a given set of conditions. Rate constants of reaction, in units of 10<SUP>6</SUP> M<SUP>−1</SUP> s<SUP>−1</SUP>, were determined to be 3 for Trp, 4 for tryptophan methyl ester, 4 for <I>N</I><SUB>b</SUB>-acetyltryptophan methyl ester, 9 for tryptamine, and 7 for <I>N</I><SUB>b</SUB>-methoxycarbonyltryptamine in the Rose Bengal-sensitized photooxidations. These values are in good agreement with those obtained from reactions with chemically generated singlet oxygen. Quenching rate constants are somewhat larger than reaction rates constants, indicating that the quenching process is the major path for the interaction of singlet oxygen with these indolic substrates. Oxidation products in chemically generated singlet-oxygen reaction of Trp are compared with those obtained from dye-sensitized photooxidations.
- 公益社団法人 日本化学会の論文
著者
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Matsuura Teruo
Department Of Materials Chemistry Faculty Of Science And Technology Ryukoku University
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Saito Isao
Department Of Cardiovascular Disease Research Eisai Tsukuba Research Laboratories
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INOUE Kenzo
Deparment of Physics, Kyushu University
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Inoue Kenzo
Department of Industrial Chemistry, Faculty of Engineering, Ehime University
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