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1990 Fiscal Year Final Research Report Summary

Development of Chemical Functions of Enzymes

Research Project

Project/Area Number 01303007
Research Category

Grant-in-Aid for Co-operative Research (A)

Allocation TypeSingle-year Grants
Research Field 有機工業化学
Research InstitutionOsaka University

Principal Investigator

OHSHIRO Yoshiki  Osaka University, Faculty of Engineering, Professor, 工学部, 教授 (70028984)

Co-Investigator(Kenkyū-buntansha) KIMURA Eiichi  Hiroshima University, School of Medicine, Professor, 医学部, 教授 (30034010)
OGOSHI Hisanobu  Kyoto University, Faculty of Engineering Professor, 工学部, 教授 (90026188)
OHNO Atsuyoshi  Kyoto University, Institute of Chemical Research, Professor, 化学研究所, 教授 (70027077)
INOUE Shohei  University of Tokyo, Faculty of Engineering, Professor, 工学部, 教授 (20010762)
AOYAMA Yasuhiro  Nagaoka University of Technology, Section of Bioorganic Chemistry, Professor, 工学部, 教授 (00038093)
Project Period (FY) 1989 – 1990
KeywordsEnzyme Models / Coenzyme Models / Molecular Recognition / Celler Recognition / Metal Complexes
Research Abstract

The research project on "Development of Chemical Functions of Enzymes" has been carried out from the viewpoints of i) construction and application of enzyme and coenzyme model systems, ii) design of highly efficient molecular recognition sites, iii) synthesis and application of biologically important metal complexes, exes, and iv) development of regulatory compounds in biological systems.
The summary of the results of the present research is as follows ; 1) Efficient model systems of quinoproteins and flavoproteins have been established and their chemical functions have been attempted to apply to organic synthesis. 2) Mechanism to differentiate stereochemistry in biological and its mimetic reaction systems has been clarified by using NAD(P)H models. 3) Model complexes of zinc enzymes have been synthesized by using several surfactants containing imidazole ligands, and their catalytic functions have been examined in ester hybrolysis. 4) Functionalized bilayer membrane has been demonstrate … More d to provide an efficient enzyme model systems. 5) "Nonselective" substrate binding via microsolvation has been first demonstrated. 6) Selective binding of enzymes and enzyme models has been achieved by using synthetic bilayer membranes. 7) Several types of functionalized porphyrin ligands have been synthesized and their chemical functions including molecular recognition ability have been investigated. 8) Heme enzyme mimetic catalyst has been developed to construct a highly efficient oxygenation systems which can be applicable to synthetic chemistry. 9) Molecular recognition sites have been designed by using zinc complexes with polyamine ligands to elucidate biometal functions. 10) Molybdo-oxidase model complexes have been synthesized and their structure and properties have been investigated. 11) Reactivities of Coordinated dinitrogen in molybdenum and tungsten complexes have ben clarified. 12) mu-Peroxo complexes of copper and iron have been prepared and their reactivities have been examined as models for oxygen carries and monooxygenases.
In order to organize the results, a meeting was held on February 5, 1991 at Osaka. It is considered that the results of each investigators have attained goal of this project judging from many outstanding findings and breakthroughs during the past two years. Less

  • Research Products

    (71 results)

All Other

All Publications (71 results)

  • [Publications] Yasuhiro Aoyama et al.: "Two-Point Hydrogen-Bonding Interaction : A Remarkable Chain-Length Selectivity in the Binding of Dicarboxylic Acids with Resorcinol-Aldehyde Cyclotetramer as a Multidentate Host" J, Am. Chem. Soc.112. 2807-2808 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yasuhiro Aoyama et al.: "Simultaneous Hydrogen Bonding and Metal Coordination Interaction in the Two-Point Fixation of Amino Acids with a Bifunctional Metalloporphyrin Receptor" J, Am. Chem. Soc.112. 3145-3151 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yasuhiro Aoyama et al.: "Highly Stereoselective Glycosidation of Ribose Solubilized in Apolar Organic Media via Host-Guest Complexation" Tetrahedron Lett.31. 6193-6196 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yasuhiro Aoyama et al.: "Molecular Recognition and Stereoselectivity : Geometrical Requirements for the Multiple Hydrogen-Bonding Interaction of Diols with a Multidentate polyhydroxy Macrocycles Y. Kikuchi, Y. Kato, Y. Tanaka, and Y. Aoyama" J. Am. Chem. Soc.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Shohei Inoue et al.: "Syntheses and Reactions of Aluminum Complexes of Capped Porphyrin" Tetrahedron. 46. 749-760 (1990)

    • Description
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  • [Publications] Shohei Inoue et al.: "Reaction of Carbon Dioxide with (Porphyrinato) aluminum Thiolates" Chem. Lett.551-554 (1990)

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  • [Publications] Shohei Inoue et al.: "Stereoselective Formation of Aluminum Enolate on Capped Prophyrin" Chem. Lett.1167-1170 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshiki Ohshiro et al.: "Preparation and Characterization of Iminoquinone and Aminophenol Derivatives of Coenzyme PQQ" Tetrahedron Lett.30,. 6875-6878 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshiki Ohshiro et al.: "Chemical Behavior of Coenzyme PQQ toward Aminoguanidine : Redox Reaction and Adduct Formation" Bull. Chem. Soc. Jpn.63. 417-420 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshiki Ohshiro et al.: "Regioselective Transformation of the Functional Groups of Coenzyme PQQ" Chem. Lett.1675-1678 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshiki Ohshiro et al.: "Oxidative Calpha-Cbeta Fission (Dealdolation) of betaーHydroxy Amino Acids by Coenzyme PQQ" J. C. S., Chem. Commun.1608-1611 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshiki Ohshiro et al.: "Amine-Oxidation Mechanism by Coenzyme PQQ" Bioorg. Chem.(1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Atsuyoshi Ohno et al.: "NAD(P)^+-NAD(P)H Models. 69. Mechanism of Stereospecific (NET)Hydride Transfer Controlled by Electronic Effect" Bull. Chem. Soc. Jpn.63. 813-818 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Atsuyoshi Ohno et al.: "NAD(P)^+-NAD(P)H Models. 71. A Convenient Route to the Synthesis of Juvabione" Bull. Chem. Soc. Jpn.63. 1255-1257 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Atsuyoshi Ohno et al.: "NAD(P)^+-NAD(P)H Models. 72. Isotope Effects to Prove the Multi-Step Mechanism in the Reduction with an NAD(P)H Analog" Bull. Chem. Soc. Jpn.63. 2682-2686 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Atsuyoshi Ohno et al.: "NAD(P)H-NAD(P)^+ Models. 73. Structure-Stereochemistry Relationship in the Reaction of NAD Analog" Bull. Chem. Soc. Jpn.64. 81-86 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Atsuyoshi Ohno et al.: "NAD(P)H-NAD(P)^+ Models. 74. Entropy-Controlled Kinetics, Stereochemistry, and Tunneling Effect" Bull. Chem. Soc. Jpn.64. 87-90 (1991)

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      「研究成果報告書概要(欧文)」より
  • [Publications] Atsuyoshi Ohno et al.: "Stereospecificity Observed in Base-Catalyzed Electrochemical Oxidation" Tetrahedron Lett.,.

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  • [Publications] Hisanobu Ogoshi et al.: "Amide Bond Scission via Bifunctional Activation with Bimetallic Porphyrin Systems with Two Different Metal Centers" Angew. Chem., Int. Ed. Engl.28. 921-922 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hisanobu Ogoshi et al.: "Binding of Amino Acids with a Bifunctional Metalloporphyrin via Concurrent Metal-Coordination and Electrostatic Interactions" Chem. Lett.1877-1880 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hisanobu Ogoshi et al.: "Novel 1 : 1 Complex of Rhodium(III)porphyrins with Nucleobases" Chem. Lett.51-54 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hisanobu Ogoshi et al.: "Simultaneous Hydrogen Bonding and Metal Coordination Interaction in the Two-Point Fixation of Amino Acids with a Bifunctional Metalloporphyrin Receptor" J. Am. chem. Soc.112. 3145-3151 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hisanobu Ogoshi et al.: "Epoxidation Reaction Catalyzed by Cyclodextrin Sandwiched Porphyrin in Aqueous Buffer Solution" J. C. S., Chem. Commun.1594-1595 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hisanobu Ogoshi et al.: "Regioselectivities and Stereoselectivities of Singlet Oxygen Generated by Cyclodextrin Sandwhiched Porphyrin Sensitization. Lipoxigenase-like Activity" J. Am. Chem. Soc.113. (1991)

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  • [Publications] Eiichi Kimura et al.: "A Novel Cyclam Appended with 3-Hydroxypyridine. An Ambident Donor Ligand Comprising a Pyridyl N and a Pyridinolate O^- Donor" Inorg. Chem.29. 4991-4996 (1990)

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  • [Publications] Eiichi Kimura et al.: "Acid Properties of Zinc(II) and Cadmium(II) in Complexation with Macrocyclic Oxo Polyamine Ligands" Inorg. Chem.29. 4621-4629 (1990)

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  • [Publications] Eiichi Kimura et al.: "A Zinc(II) Complex of 1, 5, 9, -Triazacyclododecane ([12]aneN_3) as a Model for Carbonic Anhydrase" J. Am. Chem. Soc.112. 5805-5811 (1990)

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  • [Publications] Eiichi Kimura et al.: "Mono-, Di-, and Tetrafluorinated Cyclams" J. Am. Chem. Soc.112. 9237-9245 (1990)

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  • [Publications] Toyoki Kunitake et al.: "Layered Arrangement of oriented Myoglobins in Cast Films of a Phosphate Bilayer Membrane" J. Am. Chem. Soc.112. 6744-6745 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] Toyoki Kunitake et al.: "Design of Spatial Disposition of Anionic Porphyrins in Matrices of Ammonium Bilayer Membranes" J. Am. Chem. Soc.113. 621-630 (1991)

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  • [Publications] Seiji Shinkai et al.: "Specific Inhibition of Flavin Catalyses by a "Molecular Hinge"" Tetrahedron Lett.30. 5895-5898 (1989)

    • Description
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  • [Publications] Seiji Shinkai et al.: "Coenzyme Models Part 52. Diastereo-differentiating Hydrogen Transfer in 5-Deazaflavin Oxidation of Alchols and Amines" J. C. S., Perkin Trans I,. 1075-1078 (1990)

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  • [Publications] Junzo Sunamoto et al.: "Cell Specificity of Polysaccharide Derivatives on Liposomal Surface" Chem. Lett.473-476 (1990)

    • Description
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  • [Publications] Junzo Sunamoto et al.: "The Effect of Polysaccharide Adsorption on Surface Potential of Phospholipid Monolayers Spread at Water-Air Interface" Chem. Lett.299-302 (1990)

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  • [Publications] Junzo Sunamoto et al.: "Functionlized Liposomes in Medicine" BIOmedica. 5. 31-34 (1990)

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  • [Publications] Waichiro Tagaki et al.: "Proteolytic Metalloenzyme Models in Micellar Systems" Yukagaku. 39. 744-752 (1990)

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  • [Publications] Waichiro Tagaki et al.: "Proteolytic Metalloenzyme Models in Vesicular System" J. Chem. Soc, Jpn., Chem. Ind. Chem.1080-1086 (1990)

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  • [Publications] Waichiro Tagaki et al.: "Metal-ion-facilitated Oxidations of Dihydropyridines with Molecular Oxygen and Hydrogen Peroxide" J. C. S., Perkin Trans II. 1645-1650 (1990)

    • Description
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  • [Publications] Waichiro Tagaki et al.: "Rate Enhancing Multi-site Interactions in Ester Hydrolysis Catalyzed by Cu^<2+> Complexes of Surfactant Imidazole ligands in Non-ionic Micelles" Tetrahedron Lett.31. 7023-7026 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Waichiro Tagaki et al.: "Hydrolytic Metalloenzyme Models. Micellar Effects on the Activation of the Hydroxyl Groupes of N-Alky1-2-(hydroxymetheyl)imidazole Ligands by cu^<2+> in the Transacylation of p-Nitrophenyl Picolinate" Bull. Chem. Soc. Jpn.64. 74-80 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Waichiro Tagaki et al.: "Physical and Chemical Properties of Mononuclear Cobalt Dioxygen Complexes with Tetraimidazolyl-substituted Pyridine Chelates" Bull. Chem. Soc. Jpn.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Waichiro Tagaki et al.: "Micellar Activation of Nucleophilic Cu^<2+>-complexes of Surfactant Imidazole Ligands by Cosurfactants for the Heterolysis of p-Nitrophenyl Picolinate" Chem. Lett.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Akira Nakamura et al.: "Catalytic Activity of Novel Agglomerates Composed of Fe_4S^2+_ and (Mo^VO)^<3+> Species Cross-Linked with Bulky Difunctional Ligand, 2, 4, 6-Trimethyl-1, 3-Benzenedithiolate" Makromol. Chem.191. 1807-1812 (1990)

    • Description
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  • [Publications] Akira Nakamura et al.: "Catalytic Air and Amine N-Oxide Oxidation of p-Substituted Benzoin by Molybdenum(VI) Complexes. Identification of the Deactivation Process by Dioxygen" J. C. S., Dalton Trans.387-394 (1990)

    • Description
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  • [Publications] Akira Nakamura et al.: "Activation for One-electron Reduction at Oxomolybdenum Center by Parallel Coordination of Two Cys-Pro-Leu-Cys Ligands" Chem. Lett.1781-1784 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Akira Nakamura et al.: "Synthesis and Crystal Structure of a cis-Dioxomolybdenum(VI) Complex with Two Benzenedithiolato Ligands. (NEt_4)_2[Mo^<VI>O_2(1, 2-benzenedithiolate)_2]" Chem. Lett.1655-1656 (1990)

    • Description
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  • [Publications] Akira Nakamura et el.: "Transition Metal Thiolates : Synthetic, Catalytic, and Biomimetic Aspects" Pure & Appl. Chem.62. 1011-1020 (1990)

    • Description
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  • [Publications] Akira Nakamura et el.: "O-Atom Transfer Biomimetic Oxidation of Benzoin in the Presence of Monooxomolybdenum(VI) Thiolate Complexes" J. Mol. Cata.64. 247-256 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshio Hisaeda, Yukito Murakami et al.: "Preparation and Molecular Recognition Behavior of a Hexapus Azaparacyclophane" Tetrahedron Lett.31. 1027-1030 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshio Hisaeda, Yukito Murakami et al.: "Hydrophobic Vitamin B_<12>.8. Carbon-Skeleton Rearrangement Reactions Catalyzed by Hydrophobic Vitamin B_<12> in Octopus Azaparacyclophane" Bioorg. Chem.18. 49-62 (1990)

    • Description
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  • [Publications] Yoshio Hisaeda, Yukito Murakami et el.: "Functionalized Bilayer Membranes as Artificial Tryptophan Synthase. Characterization of Catalytic Efficiency, Substrate Specificity, and Reaction Selectivity" Bull. Chem. Soc. Jpn.63. 2339-2345 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshio Hisaeda, Yukito Murakami et el.: "Enantioselective Catalysis by Artifical Tryptophan Synthase Formed with Functionalized Bilayer Membrane" Chem. Lett.1765-1768 (1990)

    • Description
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  • [Publications] Yosio Hisaeda, Yukito Murakami et al.: "Syntheses of Macrocyclic Enzyme Models. 7. Octopus Cyclophanes Having L-Asparatate Residues as Novel Water-Soluble Hosts. Aggregation Behavior and Induced-Fit Molecular Recognition" J. Am. Chem. Soc.112. 7672-7681 (1990)

    • Description
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  • [Publications] Masanobu Hidai et al.: "Novel Disilylation and Germylation of Coordinated Dinitrogen in cis-[W(N_2)_2(PMe_2PH)_4]" Chem. Lett.1303-1306 (1990)

    • Description
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  • [Publications] Masanobu Hidai et al.: "Regioselective Alkylation of Tungsten Diazoalkane Complexes via Alkenyldaizenido Complexes" J. C. S., Chem. Commun.1569-1571 (1990)

    • Description
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  • [Publications] Masanobu Hidai et al.: "Silylation of Coordinated Dinitrogen by Silylcobalt Complexes. Preparation of a New Series of Silyldiazenido and Silylhydrazido (2-) Complexes of Molybdenum and Tungsten" Chem. Lett.(1991)

    • Description
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  • [Publications] Masanobu Hidai et al.: "Regioselective Mono- and Di-C-acylation of Tungsten Diazoalkane Complexes via Alkenyldiazenido Complexes" Chem. Lett.(1991)

    • Description
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  • [Publications] Masaaki Hirobe et al.: "Highly Efficient Epoxidation of Olefins with Pyridine N-Oxides Catalyzed by Ruthenium Porphyrins" Tetrahedron Lett.30. 6545-6548 (1989)

    • Description
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  • [Publications] Masaaki Hirobe et al.: "Application of Chemical P-450 Model Systems to Study on Drug Metabolism(III). Metabolism of 3-Isobutyryl-2- isopropylpyrazolo[1, 5-a]pyridine" Chem. Pharm. Bull.38. 400-403 (1990)

    • Description
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  • [Publications] Masaaki Hirobe et al.: "Synthesis of Highly Stable Iron Porphyrin Coordinated by Alkylthiolate Anion as a Model for Cytochrome P-450 and Its Catalytic Activity in O-O Bond Cleavage" J. Am. Chem. Soc.112. 7051-7053 (1990)

    • Description
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  • [Publications] Masaaki Hirobe et al.: "Sulfide Oxidation, Amine N-Demethylation, and Olefin Oxidation by Heme-Undecapeptide, Microperoxidase-11, in the Presence of Hydrogen Peroxide" Tetrahedron Lett.31. 3163-3166 (1990)

    • Description
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  • [Publications] Masaaki Hirobe et al.: "3-Hydroxycoumarins : First Direct Preparation from Coumarins using a Cu^<2+>-Ascorbic Acid -O_2 System, and Their Potent Bioactivities." Biochem. Biophys. Res. Commun.168,. 169-175 (1990)

    • Description
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  • [Publications] Masaaki Hirobe et al.: "Increasing 5-Lipoxygenase Inhibitory Activities by Oxidative Conversion of o-Methoxyphenols Catechols using a Cu^<2+>-Ascorbic Acid-O_2 System" Chem. Pharm. Bull.38. 842-844 (1990)

    • Description
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  • [Publications] Shunich Murahashi et al.: "New Aspects of Oxypalladation of Alkenes" Acc. Chem. Res.23. 49-54 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshihiko Moro-oka et al.: "mu-eta^2 : eta^2-Peroxo Binuclear Copper Complex, [Cu(HB(3, 5-iPr_2pz)_3)]_2(O_2)" J. Am. Chem. Soc.111,. 8975-8976 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshihiko Moro-oka et al.: "Formation and Characterization of a Mononuclear (Acylperoxo)copper(II) Complex" Inorg. Chem.29. 357-358 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshihiko Moro-oka et al.: "Tetrahedral Copper(II) Complexes Supported by a Hindered Pyrazolylborate. Formation of the Thiolate Complex, Which Closely Mimics the Spectroscopic Characteristics of Blue Copper Proteins" J. Am. Chem. Soc.112. 3210-3212 (1990)

    • Description
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  • [Publications] Yoshihiko Moro-oka et al.: "Preparation and Structure of Mononuclear Iron(III) Complexes [LFeCI_3]^- and [LFe(N_3)_3]^-(L=Hydrotris-(1-pyrazolyl)borate and Hydrotris(3, 5-dimethyl-1-pyrazolyl)borate)" Inorg. Chem.29. 2868-2870 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshihiko Moro-oka et al.: "Synthetic Model for Dioxygen Binding Sites of Non-Heme Iron Proteins. X-ray Structure of Fe(OBz)(MeCN)-(HB(3, 5-iPr_2pz)_3) and Resonance Raman evidence for Reversible Formation of a Peroxo Adduct" J. Am. Chem. Soc.112. 6402-6403 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshihiko Moro-oka et al.: "Fixation of Atmospheric CO_2 by a Copper(II) Complex" J. C. S., Chem. Commun.1357-1358 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshihiko Moro-oka et al.: "Reaction Aspects of a mu-Peroxo Binuclear Copper(II) Complex" J. Am. Chem. Soc.112. 8833-8839 (1990)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1993-08-12  

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