• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Studies on Chemical Functions of Novel Redox Coenzymes

Research Project

Project/Area Number 08458177
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionOsaka University

Principal Investigator

ITOH Shinobu  Osaka University, Faculty of Engineering, Department of Applied Chemistry, Associate Professor, 工学部, 助教授 (30184659)

Co-Investigator(Kenkyū-buntansha) SUENOBU Tomoyoshi  Osaka University, Faculty of Engineering, Department of Applied Chemistry, Resea, 工学部, 助手 (90271030)
FUKUZUMI Shunichi  Osaka University, Faculty of Engineering, Department of Applied Chemistry, Profe, 工学部, 教授 (40144430)
Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥7,300,000 (Direct Cost: ¥7,300,000)
Fiscal Year 1997: ¥1,600,000 (Direct Cost: ¥1,600,000)
Fiscal Year 1996: ¥5,700,000 (Direct Cost: ¥5,700,000)
KeywordsCoenzyme / Pyrroloquinolinequione / Tryptophan Tryptophylquinone / Alcohol Dehydrogenase / Amino Dehydrogenase / Galactose Oxidase / Redox Reaction / Model Study / 補酵素モデル / 反応機構 / キノプロテイン / オルトキノン / PQQ / TTQ / モデル銅錯体 / 銅錯体
Research Abstract

In this research project, the physicochemical properties and chemical functions of novel redox coenzymes such as PQQ (pyrroloquinolinequinone) of bacterial alcohol and glucose dehydrogenases, TTQ (tryptophan tryptophylquinone) of bacterial amine dehydrogenases, and Tyr-Cys (a dimer of tyrosine and cysteine) of galactose oxidase have been explored. Followings are the summary of the results.
PQQ Project
・Model studies on quinoprotein methanol dehydrogenase has been carried out to find that the oxidation of methanol by calcium complex of coenzyme PQQ proceeds via addition-elimination mechanism. The catalytic role of calcium ion on the methanol oxidation has been also explored.
・Catalysis by calcium ion on the reoxidation of reduced PQQ by molecular oxygen has been investigated.
・Electrochemical behavior of coenzyme PQQ in aprotic organic media has been explored.
・Photochemical oxidation of benzyl alcohols by the triplet excited state of coenzyme PQQ has been explored.
・Photochemical redox react … More ions of coenzyme PQQ and related o-quinones have been investigated in detail.
・Novel addition-cyclization reaction of nitroalkane anions with o-quinone derivatives has been found to proceed via electron transfer in the charge-transfer complexes.
・TTQ Project
・Model studies of TTQ-containing amine dehydrogenases has been performed to clarify the amine oxidation mechanism by TTQ coenzyme.
・Electrostatic environment of the TTQ cofactor in methylamine dehydrogenase has been investigated by using TTQ model compounds.
・Synthesis, physicochemical properties, and amine-oxidation reaction ofindolequinone derivatives as model compounds of novel organic cofactor TTQ of amine dehydrogenases have been investigated.
Try-Cys Project
・Active site models for galactose oxidase have been developed in order to shed light on the electronic effect of the thioether group in the novel organic cofactor.
・Active site models for galactose oxidase have been developed in order to study the physicochemical properties and reactivities of copper (II) complex of the phenoxyl radical species of the novel organic cofactor. Less

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report

Research Products

(34 results)

All Other

All Publications (34 results)

  • [Publications] Shinobu Itoh et al.: "The Photochemical Oxidation of Benzyl Alcohols by the Triplet Excited State of Coenzyme Pyrroloquinonlinequinone." Chem.Commun.・4. 465-466 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh et al.: "Addition-Cyclization Reaction of Nitroalkane Anions with o-Quinone Derivatives via Electron Transfer in the Charge-transfer Complexes." J.Chem.Soc.,Perkin Trans 2. ・7. 1429-1433 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh et al.: "Electrostatic Environment of the Tryptophylquinone Cofactor in Methylamine Dehydro- genase. Evidence from Resonance Raman Spectroscopy of Model Compounds." Biochemistry. 35・15. 4713-4720 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh et al.: "Model Studies of TTQ-Containing Amine Dehydrogenases" J.Org.Chem.61・25. 8967-8974 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh et al.: "Modeling of the Chemistry of Quinoprotein Methanol Dehydrogenase. Oxidation of Methanol by Calcium Complex of Coenzyme PQQ via Addition-Elimination Mechanism." J.Am.Chem.Soc.119・2. 439-440 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh et al.: "Catalysis by Calcium Ion of the Reoxidation of Reduced PQQ by Molecular Oxygen" Chem.Commun.・1. 29-30 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh et al.: "Active Site Models for Galactose Oxidase. Electronic Effect of the Thioether Group in the Novel Organic Cofactor" Inorg.Chem.36・7. 1407-1416 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh et al.: "Synthesis,Physicochemical Properties, and Amine-Oxidation Reaction of Indolequinone Derivatives as Model Compounds of Novel Organic Cofactor TTQ of Amine Dehydrogenases." J.Org.Chem.62・17. 5898-5907 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh et al.: "Model Studies of Calcium-containing Quinoproteins Alcohol Dehydrogenaes. Catalytic Role of Ca^<2+> for the Oxidation of Alcohols by Coenzyme PQQ" Biochemistry. 37(印刷中). (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh et al.: "Development of the Active Site Model for Calcium-containing Quinoprotein Alcohol Dehydrogenases" J.Mol.Catal..in press(1998).(印刷中). (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh et al.: ""Novel Trends in Electroorganic Synthesis"(Proceedings of the 3rd International Symposium on Electroorganic Synthesis),ed.by S.Torii" Springer-Verlag,Tokyo, 15-18 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh, Takashi Komori, Yutaka Chiba, Akito Ishida, Setsuo Takamuku, and Shunichi Fukuzumi: "The Photochemical Oxidation of Benzyl Alcohols by the Triplet Excited State of Coenzyme Pyrroloquinolinequinone." Chem.Commun.(4). 465-466 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh, Junichi Maruta, and Shunichi Fukuzumi: "Addition-Cyclization Reaction of Nitroalkane Anions with o-Quinone Derivates via Electron Transfer in the Charge-transfer Complexes." J.Chem.Soc., Perkin Trans. 2 (7). 1429-1433 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Pierre.Moenne-Locoz, Nobuhumi Nakamura, Shinobu Itoh, Shunichi Fukuzumi, Antonius C.F.Gorren, Johannis A.Duine, and Joann Sanders-Loehr: "Electrostatic Environment of the Tryptophylquinone Cofactor in Methylamine Dehydroganase. Evidence from Resonance Raman Spectroscopy of Model Compounds." Biochemistry. 35 (15). 4713-4720 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh, Naoki Takada, Shigenobu Haranou, Takeya Ando, Mitsuo Komatsu, Yoshiki Ohshiro, and Shunichi Fukuzumi: "Model Studies of TTQ-Containing Amine Dehydrogenases." J.Org.Chem.61 (25). 8967-6974 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh, Hirokatsu Kawakami, and Shunichi Fukuzumi: "Modeling of the Chemistry of Quinoprotein Methanol Dehydrogenase. Oxidation of Methanol by Calcium Complex of Coenzyme PQQ via Addition-Elimination Mechanism." J.Am.Chem.Soc.119 (2). 439-440 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh, Hirokatsu Kawakami, and Shunichi Fukuzumi: "Catalysis by Calcium Ion of the Reoxidation of Reduced PQQ by Molecular Oxygen." Chem.Commun.(1). 29-30 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh, Shigehisa Takayama, Akihiro Furuta, Mitsuo Komatsu, Akito Ishida, Setsuo Takamuku, Ryuichi Arakawa, Shunichi Fukuzumi: "Active Site Models for Galactose Oxidase. Electronic Effect of the Thioether Group in the Novel Organic Cofactor." Inorg.Chem.36 (7). 1407-1416 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh, Naoki Takada, Takeya Ando, Shigenobu Haranou, Xin Huang, Yasushi Uenoyama, Yoshiki Ohshiro, Mitsuo Komatsu, and Shunichi Fukuzumi: "Synthesis Physicochemical Properties, and Amine-Oxidation Reaction of Indolequinone Derivatives as Model Compounds of Novel Organic Cofactor TTQ of Amine Dehydro-genases." J.Org.Chem.62 (17). 5898-5907 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh, Hirokatsu Kawakami, and Shunichi Fukuzumi: "Model Studies of Calcium-containing Quinoproteins Alcohol Dehydrogenaes. Catalytic Role of Ca^<2+> for the Oxidation of Alcohols by Coenzyme PQQ." Biochemistry. 37 (in press). (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh, Hirokatsu Kawakami, and Shunichi Fukuzumi: "Development of the Active Site Model for Calcium-containing Quinoprotein Alcohol Dehydrogenases." J.Mol.Catal.(in press). (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh, Hirokatsu Kawakami, and Shunichi Fukuzumi: Redox Catalysis of Novel Heterocyclic o-Quinone Coenzymes."Novel Trends in Electroorganic Synthesis", ed.by S.Torii, Springer-Verlag, Tokyo, 15-18 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinobu Itoh et al.: "Modeling of the Chemistry of Quinoprotein Methanol Dehydrogenase. Oxidation of Methanol by Calcium Complex of Coenzyme PQQ via Addition-Elimination Mechanism." J.Am.Chem.Soc.119・2. 439-440 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Shinobu Itoh et al.: "Catalysis by Calcium Ion of the Reoxidation of Reduced PQQ by Molecular Oxygen" Chem.Commun.・1. 29-30 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Shinobu Itoh et al.: "Active Site Models for Galactose Oxidase. Electronic Effect of the Thioether Group in the Novel Organic Cofactor" Inorg.Chem.36・7. 1407-1416 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Shinobu Itoh et al.: "Synthesis,Physicochemical Properties,and Amine-Oxidation Reaction of Indolequinone Derivatives as Model Compounds of Novel Organic Cofactor TTQ of Amine Dehydrogenases." J.Org.Chem.62・17. 5898-5907 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Shinobu Itoh et al.: "Mechanistic Studies of Aliphatic Ligand Hydroxylation of a Copper Complex by Dioxygen : A Model Reaction for Copper Monooxygenases" J.Am.Chem.Soc.120・(印刷中). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Shinobu Itoh et al.: "Model Studies of Calcium-containing Quinoproteins Alcohol Dehydrogenases. Catalytic Role of Ca^<2+> for the Oxidation of Alcohols by Coenzyme PQQ" Biochemistry. 37・(印刷中). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Shinobu Itoh et al.: "The Photo chemical Oxidation of Benzyl Alcohols by the Triplet Excited state of Coenzyme Pyrroloquinolinequinone" Chem.Commun.(4). 465-466 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Shinobu Itoh et al.: "Addition-Cyclization Reaction of Nitoroalkane Anions with 0-Quinone Derivatives via Electron Transfer in the C-T Complexes" J.Chem.Soc.,Perkin Trans.2. (7). 1429-1433 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Shinobu Itoh et al.: "Electronic Environment of the Trytophylquinone Cofactor in Methylamine Dehydrogenase. Evidence from Resonance Ramman" Biochemistry. 35(15). 4713-4720 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Shinobu Itoh et al.: "Model Studies of TTQ-Containing Amine Dehydrogenases" J.Org.Chem.61(25). 8967-8974 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Shinobu Itoh et al.: "Modeling of the Chemistry of Quinoprotein Methanol Dehydrogenase Oxidation of Methanol by Calcium Complex of Coenzyme PQQ・・・" J.Am.Chem.Soc.119(2). 439-440 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] Shinobu Itoh et al.: "Catalysis of Calcium Ion of the Reoxidation of Reduced PQQ by Molecular Oxygen" Chem.Commun.(1). 29-30 (1997)

    • Related Report
      1996 Annual Research Report

URL: 

Published: 1996-03-31   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi