Catharanthine Oxidation in Flavin Mononucleotide-Mediated Catharanthine-Vindoline Coupling Reaction for Synthesis of Dimeric Indole Alkaloids under Near-Ultraviolet Light

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概要

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• A reaction model for the flavin mononucleotide-mediated coupling of catharanthine(C)and vindoline(V)under near-ultraviolet light was established based on the results of experiments on the effects of various physical and chemical factors on the disappearance of C and V, and the synthesis of the product, a dihydropyridinium intermediate(IM). The following events were deduced to occur. (i)C is oxidized in the presence of FMN and oxygen under near-ultraviolet light(C_<OX1>). (ii)C_<OX1> then couples with V to form IM. Degradation of C occurs simultaneously with its specific oxidation, as a result of which a part of the C is converted into the product(C^*)which is incapable of coupling with V. When a reaction in which C_<OX1> is further oxidized to another form(C_<OX2>)is added and the counterpart for the coupling with V is changed to C_<OX2> from C_<OX1> the reaction model more appropriately describes the exponential increase in the product, IM, that occurs in the early stage of the coupling reaction. (iii)The degradation rate of IM is much greater after C has been consumed than before its disappearance. Using this reaction model, the coupling reactions under basal and optimized conditions were simulated and the results showed a good fit with the experimental values under both conditions. The kinetic study suggests that manganese ion(Mn^<2+>)stimulates the binding of C_<OX2> with V in addition to suppressing the degradation of C, resulting in an increased yield of IM. Mn^<2+> thus appears to be an important factor in the coupling reaction, in which it plays two different roles.

• 社団法人日本生物工学会の論文
• 1999-06-25

著者

• Hirata Kazumasa

  Applied Environmental Biology Graduate School Of Pharmaceutical Sciences Osaka University

• Hashimoto K

  Environmental Bioengineering Laboratory Graduate School Of Pharmaceutical Sciences Osaka University

• HIRATA KAZUMASA

  Environmental Bioengineering Laboratory, Graduate School of Pharmaceutical Sciences, Osaka Universit

• MIYAMOTO KAZUHISA

  Environmental Bioengineering Laboratory, Graduate School of Pharmaceutical Sciences, Osaka Universit

• Miyaoku Kohei

  Department Of Synthetic Chemistry And Biological Chemistry Graduate School Of Engineering Kyoto Univ

• HONDA MOTOYASU

  Environmental Science and Microbiology, Faculty of Pharmaceutical Sciences, Osaka University

• Hirata Kazumasa

  Department Of Biochemical Engineering Faculty Of Pharmaceutical Sciences Osaka University

• Hirata Kazumasa

  Environmental Bioengineering Laboratory Graduated School Of Pharmaceutical Sciences Osaka University

• Hirata Kazumasa

  Environ. Bioeng. Lab Grad. Sch. Pharm. Sci. Osaka Univ.

• Miyamoto Kazuhisa

  Environmental Bioengineering Laboratory Graduate School Of Pharmaceutical Sciences Osaka University

• Miyamoto Kazuhisa

  Environmental Bioengineering Laboratory Graduated School Of Pharmaceutical Sciences Osaka University

• Miyamoto Kazuhisa

  Laboratory Of Biological Defenoe Department Of Insect Physiology And Behavior National Institute Of

• Duangterappecha Supanee

  Environmental Bioengineering Laboratory Graduate School Of Pharmaceutical Sciences Osaka University

• Miyamoto K

  Environmental Biotechnology Laboratory Graduate School Of Pharmaceutical Sciences Osaka University

• AKAGI TOMOHIRO

  Environmental Bioengineering Laboratory, Graduate School of Pharmaceutical Sciences, Osaka Universit

• DUANGTERAPRECHA SUPANEE

  Environmental Bioengineering Laboratory, Graduate School of Pharmaceutical Sciences, Osaka Universit

• SAKAMOTO YAYOI

  Environmental Bioengineering Laboratory, Graduate School of Pharmaceutical Sciences, Osaka Universit

• NAGSE HIROYASU

  Environmental Bioengineering Laboratory, Graduate School of Pharmaceutical Sciences, Osaka Universit

• Honda M

  Gifu Prefectural Inst. Bioindustrial Technol. Gifu Jpn

• Honda Motoyasu

  Environmental Science And Microbiology Faculty Of Pharmaceutical Sciences Osaka University

• Akagi Tomohiro

  Environmental Bioengineering Laboratory Graduate School Of Pharmaceutical Sciences Osaka University

• Sakamoto Yayoi

  Environmental Bioengineering Laboratory Graduate School Of Pharmaceutical Sciences Osaka University

• Nagse Hiroyasu

  Environmental Bioengineering Laboratory Graduate School Of Pharmaceutical Sciences Osaka University

• Hirata K

  Environmental Biotechnology Laboratory Graduate School Of Pharmaceutical Sciences Osaka University

• Miyamoto K

  Faculty Of Pharmaceutical Sciences Osaka University

• Hirata Kazumasa

  Osaka Municipal Technical Research Institute

• Miyamoto Kazuhisa

  Environmental Bioengineering Laboratory Faculty Of Pharmaceutical Sciences Osaka University

• HONDA MOTOYASU

  Environmental Bioengineering Laboratory, Graduate School of Pharmaceutical Sciences, Osaka University

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