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1996 Fiscal Year Final Research Report Summary

Application of DMSO reductase to asymmetric synthesis and its large scale praparation of the enzyme.

Research Project

Project/Area Number 07556027
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section試験
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

YAMAZAKI Sunao  Univ.of Tokyo, dept.of Applied Biochemistry, Professor, 大学院・農学生命科学研究科 (00011982)

Co-Investigator(Kenkyū-buntansha) YOSHIMURA Etsuro  Univ.of Tokyo, dept.of Appl.Biochem., Assoc.Professor, 大学院・農学生命科学研究科, 助教授 (10130303)
OKUBO Akira  Univ.of Tokyo, dept.of Appl.Biochem., Assoc.Professor, 大学院・農学生命科学研究科, 助教授 (20111479)
SATOH Toshio  Hiroshima, Univ., Fac.of Sci., Professor, 理学部, 教授 (90087130)
Project Period (FY) 1995 – 1996
KeywordsDMSO reductase / Rhodobacter sphaeroides / reduction of sukfoxide / reduction of N-oxide / asymmetric synthesis / stereoselective synthesis
Research Abstract

Dimethyl sulfoxide reductase (DMSO-R) isolated from the photosynthetic denitrifyingbacterium, Rhodobacter sphaeroides f.sp. denitrificans, reduces not only varieties of sulfoxides to the corresponding sulfides but also N-oxides to their reduced forms. In the case of sulfoxide reduction, the enzyme recognizes the stereochemistry of asymmetric sulfoxides, i.e., (S) -methylphenylsulfoxide (MPSO) of the racemic mixtureis exclusivelyreduced to the sulfide and 100% e.e.(R) isomer is recovered. MPSO and other alkylaryl sulfoxides (RArSO) were synthesized and assayd for the stereoselectivity of DMSO-R as well as for the kinetic parameters, Vmax and Km. Reaction rate was well monitored by capillary electrophoresis using the micellar electrokinetic chromatographic mode. Stereospecific reaction pattern of the enzyme was clearly solved for the synthesized substrates, RArSO.Three preparative methods to obtain optically pure sulfoxides were examined : (1) reduction by in vitro enzyme reaction which requires pure enzymes ; (2) biotransformation by adding substrates to the culture of Rhodobacter sphaeroides in which DMSO-R was beforehand induced and (3) reduction in bioreactor using immobilized DMSO-R.MTSO and methyltolylsulfoxide (MTSO) which are important intermediates for the asymmetric organic synthesis were applied to the method (2) and optically pure (R) isomers were obtained in gram-order yield.

  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] 佐藤, 佐々木, 大久保, 田之倉, 山崎: "Crystallization and Preliminavy Crystallographic Studies of DMSO reductase from R.sphaeroides." Proc.Japan Acad.73B. 30-32 (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 安保, 大久保, 山崎: "Preparoitive Aoymmetric Deoxygenation of Alkyl Aryl Sulfoxides by Rhodobacter sphaeroides." Tetrahedron : Asymmetry. 8. 345-348 (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Ujiie, T.Saitoh, S.Yamazaki 他: "Nucleofide Sequence of the gene encoding the penta heme cyto dnume and the trous membrane protein involved in DMSO respivation" Biochim.Biophys.Aeta. 1227. 1-5 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Matsuzaki et al.: "Stobilization by GroEL,a Molecular Chaperone and a Periplannic Function" Plant Cell Physiol.37. 333-339 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 安保 充 他: "ジメチルスルフォキシド還元酵素によるスルフォキシドの速度論的分割" 分析化学. 44. 835-838 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Abo et.al.: "Enantio selective Deoxigemation of Alkyl Aryl Sulfoxides・・" Bioorg.Med.Chem.3. 109-112 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Tachibana, H.Onoe, A.Okubo, S.Yamazaki: ""Application of Micellar Electrokinetic Chromatography as a Novel Assay Method for Dimethyl Sulfoxide Reductase"" Biosci.Biotech.Biochem. 59. 282-284 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] I.Yamamoto, N.Wada, T.Ujiiye, M.Tachibana, M.Matsuzaki, H.Kajiwara, Y.Watanabe, H.Hirano, A.Okubo, T.Satoh and S.Yamazaki: ""Cloning and Nucleotide Sequence of the Gene Encoding Dimethyl Sulfoxide Reductase from Rhodobacter sphaeroides f.sp.denitrificans."" Biosci.Biotech.Biochem.59. 1850-1855 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Abo, M.Tachibana, A.Okubo and S.Yamazaki: ""Enantioselective Deoxygenation of Alkyl Aryl Sulfoxides by DMSO Reductase from Rhodobacter sphaeroides f.s.denitrificans."" Bioorg.Med.Chem.3. 109-112 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Matsuzaki, Y.Yamaguchi, H.Masui and T.Satoh: ""Stabilization by GroEL,a Molecular Chaperone, and a Periplasmic Fraction as Well as Refolding in the Presence of Dithiothreitol, of Acid-Unfolded Dimethyl Sulfoxide Reductase, a Periplasmic Protein of Rhodobacter sphaeroides f.sp.denitrificans."" Plant Cell Physiology. 37. 333-339 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Ujiiye, I.Yamamoto, H.Nakama, A.Okubo, S.Yamazaki, T.Satoh: ""Nucleotide sequence of the genes, encoding the pentaheme cytochrome (dmsC) and the transmembrane protein (dmsB), involved in dimethyl sulfoxide respiration from Rhodobacter sphaeroides f.sp.denitrificans."" Biochim.Biophys.Acta. 1277. 1-5 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Abo, A.Okubo and S.Yamazaki: ""Preparative Asymmetric deoxygenation of alkyl aryl sulfoxides by Rhodobacter sphaeroides f.sp.denitrificans."" Tetrahedron : Asymmetry. 8. 345-348 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Sato, H.Sasaki, A.Okubo, M.Tanokura and S.Yamazaki: ""Crystallization and Preliminary Crystallographic Studies of Dimethyl Sulfoxide Reductase from Rhodobacter sphaeroides f.sp.denitrificans."" Proc.Japan Acad.73, Ser.B. 30-32 (1997)

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

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Published: 1999-03-16  

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