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A Model System for Pyridoxal Phosphate-catalyzed Reaction.

Research Project

Project/Area Number 09672198
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Physical pharmacy
Research InstitutionKyoritsu College of Pharmacy

Principal Investigator

MATSUSHIMA Yoshikazu  Kyoritsu College of Pharmacy, Faculty of Pharmaceutical Sciences, Professor (60037603)

Project Period (FY) 1997 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 1999: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1998: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1997: ¥2,600,000 (Direct Cost: ¥2,600,000)
Keywordspyridoxal / pyridoxamine / quinonoide / ketimine / Al(III) chelate / Cu(III) chelate / aldimine
Research Abstract

1. Course of the formation of a quinonoid species absorbing in the 500-nm region, which should serve as a model for the key intermediate in reaction catalyzed by pyridoxal phosphate enzymes, was studied in the reaction of pyridoxal, ethyl L-alaninate and Al(III) in methanol by means of UV-visible spectroscopy, chromatography with a multi-UV detector, optical rotation and ^1H-NMR. The species was chromatographically separated in the form of the Al(III) chelate and its quantitative transformation to the aldimine chelate was observed. The formation of the species in the transamination reaction of pyridoxamine, ethyl pyruvate and A1(III) was also studied.
2. Quinonoide species absorbing in the 500-nm region, which should serve as a model for the key intermediate in reaction catalyzed by pyridoxal phosphate enzymes, was observed in the reaction of pyridoxalmine (PM) with pyrroloquinoline quinine (PQQ), 1,7-phenathroline-5,6-quinone and 4,7-phenathroline-5,6-quinone in alkaline methanol at 25℃. Crystalline product was prepared from PM and PQQ. This may be the first example of meta-stable quinonoid species in pyridoxal catalysis which are not in the form of metal chelate.
3. By the formation of the hexacoordinated mixed chelate, the Cu(II)-quinonoid-ligand should retard the protonation of the quinonoid to convert to the aldimine, as clearly observed in the reaction of α,α',α"-terpyridine. Although the reasons for these phenomena are not fully understood at this stage, the decrease of the carbanion property of the quinonoid by effective chelation to polyvalent metal ions may hinder protonation. The stability of the quinonoid chelate may be enhanced by the formation of mixed chelates with the strongly chelating tridentate planar ligand. The results indicated that the stability of the chelate was determined not only by the interaction of the metal and the quinonoid, but also by the interaction of the metal with the other ligands.

Report

(4 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report
  • 1997 Annual Research Report
  • Research Products

    (12 results)

All 1999 1998 1997 Other

All Journal Article (6 results) (of which Peer Reviewed: 3 results) Presentation (2 results) Publications (4 results)

  • [Journal Article] Species absorbing in the 500-nm region, in the reactions of pyridoxamine with pyrroloquinoline quinine.1999

    • Author(s)
      Nagata Y, Matsushima Y, et al.
    • Journal Title

      Chem.Pharm.Bull. 47(12)

      Pages: 1774-1777

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Species absorbing in the 500-nm region, in the reactions of pyridoxamine with pyrroloquinoline quinine1999

    • Author(s)
      Nagata Y, Matsushima Y, et al.
    • Journal Title

      Chem.Pharm.Bull. 47(12)

      Pages: 1774-1777

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Journal Article] Intermediate species absorbing in the 500-nm region in Al(III)catalyzed nonenzymatic transamination.1998

    • Author(s)
      Nagata Y, Yoda R, Matsushima Y.
    • Journal Title

      Chem.Pharm.Bull. 46(12)

      Pages: 1849-1852

    • NAID

      110003616819

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Intermediate species absorbing in the 500-nm region in Al(III)catalyzed nonenzymatic transamination1998

    • Author(s)
      Nagata Y, Yoda R, Matsushima Y.
    • Journal Title

      Chem.Pharm.Bull. 46(12)

      Pages: 1849-1852

    • NAID

      110003616819

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Journal Article] A uinonoid intermediate species absorbing in the 500-nm region in Al(III)catalyzed pyridoxal catalysis.1997

    • Author(s)
      MATSUSHIMA Y.
    • Journal Title

      Journal of Inorganic Biochemistry 67

      Pages: 307-307

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] A quinonoid intermediate species absorbing in the 500-nm region in Al(III)catalyzed pyridoxal catalysis1997

    • Author(s)
      MATSUSHIMA Y.
    • Journal Title

      Journal of Inorganic Biochemistry 67

      Pages: 307-307

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Presentation] A quinonoid intermediate species absorbing in the 500-nm region in Al(III)catalyzed pyridoxal catalysis.1997

    • Author(s)
      Matsushima Y, Nagata Y.
    • Organizer
      8^<th> International Conference on Bioinorganic Chemistry
    • Place of Presentation
      Yokohama
    • Year and Date
      1997-07-27
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Presentation] A quinonoid intermediate species absorbing in the 500-nm region in Al(III)catalyzed pyridoxal catalysis1997

    • Author(s)
      Matsushima Y, Nagata Y.
    • Organizer
      8^<th> International Conference on Bioinorganic Chemistry
    • Place of Presentation
      Yokohama
    • Year and Date
      1997-07-27
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Nagata Y,Yoda R,Matsushima Y,: "Intermediate species absorbing in the 500-nm region in Al(III)-catalyzed nonenzymatic transamination"Chem. Pharm. Bull.. 46(12). 1849-1852 (1998)

    • Related Report
      1999 Annual Research Report
  • [Publications] Nagata Y,Matsushima Y,他: "Species absorbing in the 500-nm region, in the reactions of Pyridoxamine with Pyrroloquinoline quinone."Chem. Pharm. Bull.. 47,(12). 1747-1777 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Nagata Y,Yoda R,Matsushima Y: "Intermediate species absorbing in the 500-nmregion in Al(III)catalyzed nonenzymatic transamination" Chem.Pharm.Bull.46(12). 1849-1852 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] MATUSHIMA Y: "A quinonoid intermediate species absorbing in the 500-nm region in Al(III)catalyzed pyridoxal catalysis" Journal of Inorganic Biochemistry. 67. 307 (1997)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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