65853-81-8Relevant academic research and scientific papers
DYE-SENSITIZED PHOTOOXYGENATION OF TRYPTOPHAN: 3a-HYDROPEROXYPYRROLOINDOLE AS A LABILE PRECURSOR OF FORMYLKYNURENINE
Nakagava, Masako,Kato, Shiro,Kataoka, Shigehiro,Kodato, Shinichi,Watanabe, Hideyuki,et al.
, p. 1013 - 1026 (2007/10/02)
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 apprpopiate conditions, was easily convertible to formylkynurenine.Plausible mechanisms for these transformations are discussed.Keywords-tryptophan and its derivatives; dye-sensitized photooxygenation; formylkynurenine; hydroperoxypyrroloindoles; 3-hydroperoxyindolenines; 1,3-benzoxazines; CD spectra; rearrangement; ring-chain tautomerism; biological oxidation
