Superoxide-Mediated Oxygenation of Tryptophan Analogues

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概要

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• Oxygenation of tryptophan analogues, 2-(3-indolyl) acetic acid (1), 3-(3-indolyl) propionic acid (2), N-benzoyl-L-tryptophan (3), N-tert-butoxycarbonyl-L-tryptophan (4), and N-benzoyl-L-tryptophan n-butylamide (5), with potassium superoxide (KO_2) in dimethyl sulfoxide have been studied. In the case of 1, the major products were 2-formylaminobenzoic acid (25. 3%) and 2'-formylaminoacetophenone (18. 0%), which were produced by the secondary oxidation of 3-(2-formylaminophenyl)-3-oxopropinoic acid. The reaction of 2 with O_2 ^- afforded 4-(2-formylaminophenyl)-4-oxobutanoic acid as the major product (43. 3%), and 2-(3-dioxindolyl) acetic acid (14. 5%) was also obtained. The reaction of 3 and 4 afforded 2-benzoylamino-4-(2-formylaminophenyl)-4-oxobutanoic acid (42. 1%) and 2-tert-butoxycarbonylamino-4-(2-formylaminophenyl)-4-oxobutanoic acid (95. 7%) as the major products, respectively. In the case of 3, 1-benzoyl-2-carboxy-3a-hydroxy-1, 2, 3, 3a, 8, 8a-hexahydropyrrolo[2, 3-b]indole (27. 4%) was also obtained. Unlike 3 and 4, the reaction of 5 mainly afforded N-n-butyl-2-benzoylamino-3-(3-dioxindolyl)propanamide (15) (52. 4%). We found that 1-n-butyl-2-oxo-3-benzoylamino-4a-hydroxy-1, 2, 3, 4, 4a, 9, 9a-heptahydropyrido[2, 3-b]indole is a precursor of 15. A similar difference in the reactivity between 3, 4, and 5 was also observed for two tryptophan-containing dipeptides, N-acetyl-glycyl-L-tryptophan and N-acetyl-L-tryptophyl-glycine.

• 社団法人日本農芸化学会の論文
• 1994-03-23

著者

• UCHIDA Koji

  Laboratory of Food and Biodynamics, Nagoya University School of Agriculture

• Uchida K

  Nagoya Univ. Nagoya Jpn

• Uchida Koji

  名古屋大学 生命農学研究科

• Uchida Kanako

  Department Of Applied Biological Chemistry Graduate School Of Agricultural And Life Sciences The Uni

• KAWAKISHI Shunro

  Laboratory of Food and Biodynamics, Department of Applied Biological Sciences, Nagoya University

• Uchida Koji

  Laboratory Of Food And Biodynam Ics Department Of Applied Biological Sciences Nagoya University

• Itakura Koichi

  Laboratory Of Food And Biodynam Ics Department Of Applied Biological Sciences Nagoya University

• Uchida Koji

  Laboratory Of Food And Biodynamics Nagoya University School Of Agriculture

• Kawakishi S

  Nagoya University

• Kawakishi Shunro

  Laboratory Of Food And Bio-dynamics Nagoya University

• Uchida Koji

  Laboratory of Food and Biodynamics, Nagoya University School of Agricultural Science

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