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Synthesis of water-soluble selenium reagents and their applications to protein chemistry

Research Project

Project/Area Number 13640525
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

IWAOKA Michio  The University of Tokyo, Graduate School of Arts and Sciences, Research Associate, 大学院・総合文化研究科, 助手 (30221097)

Project Period (FY) 2001 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2002: ¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 2001: ¥1,600,000 (Direct Cost: ¥1,600,000)
Keywordsselenium / protein / redox / disulfide bond / folding / 酸化還元剤 / 酸化還元試剤
Research Abstract

For folding study of proteins with disulfide bonds (SS bonds), water soluble sulfur reagents are normally used. In this research project, new selenium compounds have been synthesized and applied to oxidative folding experiments of proteins. This study is based on a general chemical concept that selenium is more redox-acitive than sulfur.
Two-types of water-soluble selenium reagents were synthesized. When one of the reagents was used for folding experiments, the reagent reacted with a reduced form of bovine pancreatic ribonuclease A rapidly (within 10 sec) and quantitatively to form protein SS bonds. To investigate details of the rapid processes, a quench-flow equipment was constructed. The kinetic experiments using the quench-flow equipment revealed that the reaction between the protein and the selenium reagent completes within 1 sec and also that the SS formation proceeds during 50 to 100 msec. The results suggested that the selenium reagent may be able to trap folding intermediates that are formed rapidly in the beginning of folding and are alive in a short period. Thus, the selenium reagents would be useful for oxidative folding study of proteins.
In this research project, database analysis of weak interactions in PDB and ab initio molecular orbital calculations of single amino acids have been also carried out. S…O interactions were discovered in protein structures. Conformational preferences of a single amino acid in water were suggested to be important in the folding of a polypeptide chain to secondary structures.

Report

(3 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • Research Products

    (40 results)

All Other

All Publications (40 results)

  • [Publications] Michio Iwaoka: "trans-3,4-Dihydroxy-1-Selenolane Oxide. A New Reagent for Rapid and Quantitative Formation of Disulfide Bonds in Polypeptides"Chem. Lett.. 1400-1401 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Statistical Characterization of Nonbonded S・・・O Interactions in Proteins"Chem. Lett.. 132-133 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Synthesis and Structural Characterization of Water-Soluble Selenium Reagents for the Redox Control of Protein Disulfide Bonds"Heteroatom. Chem.. 12. 293-299 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Daisuke Kaneno: "π-Facial Diastereoselection of Hydride Reduction of 1,3-Diheteran-5-ones. Application of the Exterior Frontier Orbital Extension Model"Heteroatom. Chem.. 12. 358-368 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Takanori Harada: "Implications of Intramolecular OH・・・Se Hydrogen Bonding and CH・・・O Interaction in the Conformational Stabilization of 2-(Methylseleno)ethanol Studied by Vibrational Spectroscopy and Density Functional Theory"Heteroatom. Chem.. 105. 4517-4523 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Osamu Takahashi: "Hydrogen-bonding Nature of the CH/π Interaction as Evidenced by Crystallographic Database Analyses and ab initio Molecular Orbital Calculations"Heteroatom. Chem.. 74. 2421-2430 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 岩岡道夫: "高選択的かつ高効率的なペプチドSS結合の生成試剤"化学と工業. 54. 684-684 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Quantitative Evaluation of Weak Nonbonded Se・・・F Interactions and Their Remarkable Nature as Orbital Interactions"J. Am. Chem. Soc.. 124. 1902-1909 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Solvent Effects on the φ-ψ Potential Surfaces of Glycine and Alanine Dipeptides Studied by the PCM and I-PCM Methods"J. Mol. Stuct.(THEOCHEM). 586. 111-124 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Heavy-Row Atom Effects on the Strength of the Weak Nonbonded Interactions between Divalent Selenium and Halogen Atoms"Chem. Lett.. 518-519 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Weak Nonbonded S・・・X (X=O, N, and S) Interactions in Proteins. Statistical and Theoretical Studies"Bull. Chem. Soc. Jpn.. 75. 1611-1625 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Statistical and Theoretical Investigations on the Directionality of Nobonded S O Interactions. Implications for Molecular Design and Protein Engineering"J. Am. Chem. Soc.. 124. 10613-10620 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "The SAAP Force Field. A Simple Approach to a New All-Atom Protein Force Field by Using Single Amino Acid Potential (SAAP) Functions in Various Solvents"J. Comput. Chem.. (in press). (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 岩岡道夫: "非結合性S・・・O相互作用の方向性に関する統計的および理論的研究.分子設計とタンパク質工学における意義"ゲノムニュース. 第5号. 29-31 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "trans-3,4-Dihydroxy-1-Selenolane Oxide. A New Reagent for Rapid and Quantitative Formation of Disulfide Bonds in Polypeptides"Chem. Lett.. 1400-1401 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Statistical Characterization of Nonbonded S…O Interactions in Proteins"Chem. Lett.. 132-133 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Synthesis and Structural Characterization of Water-Soluble Selenium Reagents for the Redox Control of Protein Disulfide Bonds"Heteroatom Chem.. 12. 293-599 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Daisuke Kaneno: "π-Facial Diastereoselection of Hydride Reduction of 1,3-Diheteran-5-ones. Application of the Exterior Frontier Orbital Extension Model"Heteroatom Chem.. 12. 358-368 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Takanori Harada: "Implications of Intramolecular OH…Se Hydrogen Bonding and CH…O Interaction in the Conformational Stabilization of 2-(Methylseleno)ethanol Studied by Vibrational Spectroscopy and Density Functional Theory"J. Phys. Chem. A. 105. 4517-4523 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Osamu Takahashi: "Hydrogen-bonding Nature of the CH/π Interaction as Evidenced by Crystallographic Database Analyses and ab initio Molecular Orbital Calculations"Bull. Chem. Soc. Jpn.. 74. 2421-2430 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Highly Selective and Highly Efficient Reagents for Prptide Disulfide Bond Formation"Chemistry and Chemical Industry. 54. 684 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Quantitative Evaluation of Weak Nonbonded Se…F Interactions and Their Remarkable Nature as Orbital Interactions"J. Am. Chem. Soc.. 124. 1902-1909 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Solvent Effects on the φ-ψ Potential Surfaces of Glycine and Alanine Dipeptides Studied by the PCM and I-PCM Methods"J. Mol. Struct. (THEOCHEM). 586. 111-124 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Heavy-Row Atom Effects on the Strength of the Weak Nonbonded Interactions between Divalent Selenium and Halogen Atoms"Chem. Lett. 518-519 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Weak Nonbonded S…X (X = O, N, and S) Interactions in Proteins. Statistical and Theoretical Studies"Bull. Chem. Soc. Jpn.. 75. 1611-1625 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Statistical and Theoretical Investigations on the Directionality of Nonbonded S…O Interactions. Implications for Molecular Design and Protein Engineering"J. Am. Chem. Soc.. 124. 10613-10620 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "The SAAP Force Field. A Simple Approach to a New All-Atom Protein Force Field by Using Single Amino Acid Potential (SAAP) Functions in Various Solvents"J. Comput. Chem.. in press. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Statistical and Theoretical Investigations on the Directionality of Nonbonded S…O Interactions. Implications for Molecular Design and Protein Engineering"Genome News. No. 5. 29-31 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Michio Iwaoka: "Quantitative Evaluation of Weak Nonbonded Se…F Interactions and Their Remarkable Nature as Orbital Interactions"J. Am. Chem. Soc.. 124. 1902-1909 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Michio Iwaoka: "Solvent Effects on the φ-ψ Potential Surfaces of Glycine and Alanine Dipeptides Studied by the PCM and I-PCM Methods"J. Mol. Struct.(THEOCHEM). 586. 111-124 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Michio Iwaoka: "Heavy-Row Atom Effects on the Strength of the Weak Nonbonded Interactions between Divalent Selenium and Halogen Atoms"Chem. Lett.. 518-519 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Michio Iwaoka: "Weak Nonbonded S…X(X = O, N, and S) Interactions in Proteins. Statistical and Theoretical Studies"Bull. Chem. Soc. Jpn.. 75. 1611-1625 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Michio Iwaoka: "Statistical and Theoretical Investigations on the Directionality of Nonbonded S…O Interactions. Implications for Molecular Design and Protein Engineering"J. Am. Chem. Soc.. 124. 10613-10620 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Michio Iwaoka: "The SAAP Force Field. A Simple Approach to a New All-Atom Protein Force Field by Using Single Amino Acid Potential (SAAP) Functions in Various Solvents"J. Comput. Chem.. (accepted). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Michio Iwaoka: "Statistical Characterization of Nonbonded S・・・0 Interactions in Proteins"Chemistry Letters. 132-133 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Michio Iwaoka: "Synthesis and Structural Characterization of Water-Soluble Selenium Reagents for the Redox Control of Protein Disulfide Bonds"Heteroatom Chemistry. 12. 293-299 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] 岩岡 道夫: "高選択かつ高効率的なペプチドSS結合の生成試剤"化学と工業. 54. 684 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Osamu Takahashi: "Hydrogen-bonding Nature of the CH/pi Interaction as Evidenced by Crystallographic Database Analyses and ab initio Molecular Orbital Calculations"Bulletin of the chemical Society of Japan. 74. 2421-2430 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Michio Iwaoka: "Quantitative Evaluation of Weak Nonbonded Se・・・F Interactions and Their Remarkable Nature as Orbital Interactions"Journal of the American Chemical Society. (in press). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Michio Iwaoka: "Solvent Effects on the Phi-Psi Potential Surfaces of Glycine and Alanine Dipeptides Studied by the PCM and I-PCM Methods"Journal of Molecular Structure (THEOCHEM). (accepted). (2002)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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