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1993 Fiscal Year Final Research Report Summary

C-P compounds, biological activities and medical uses.

Research Project

Project/Area Number 04304049
Research Category

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

Allocation TypeSingle-year Grants
Research Field 医学一般
Research InstitutionNiigata University

Principal Investigator

SATAKE Mei  Niigata University, Brain Research Institute, Professor, 脳研究所, 教授 (70018589)

Co-Investigator(Kenkyū-buntansha) YAMASHITA Mitsuji  Shizuoka University, Faculty of Engineering, Associate Professor, 工学部, 助教授 (60110748)
SETO Haruo  Tokyo University, Institute of Modecular and Cellular Science, Professor, 分子細胞生物学研究所, 教授 (10013335)
HAYASHI Akira  Kinki University, Faculty of Science and Technology, Professor, 理工学部, 教授 (20088313)
SUGITA Mutsumi  Siga University, Faculty of Liberal Arts and Education, Professor, 教育学部, 教授 (20024937)
Project Period (FY) 1992 – 1993
KeywordsC-P compounds / Glycolipids / Nervous tissues / Antibiotics / Enzymatic synthesis of C-P bond / Genes / Chemical synthesis of C-P compounds
Research Abstract

Since Horiguchi and Kandatsu first isolated natural C-P compound, 2-aminoethyl-phosphonate, much work has been carried out in Japan. Theme of the present 2-years project were (1) isolation and identification, (2) tissue distribution, (3) biological activities, (4) biosynthesis and (5) chemical synthesis of the C-P compounds.
Following results were obtaied : (Theme 1) Several new C-P sphingoglycolipids were isolated from protostomia. Their carbohydrate and oligosaccharide structures were different from those of deuterostomia. A glycolipid had one mole each of 2-aminoethylphosphonate (C-P) and phosphoethanolamine (C-O-P) which suggests a way of molecular evolution of sphingoglycolipid species. (Theme 2) antiphosphonoglycocerebroside antisera specifically stain nervous tissues of crustacea. (Theme 3) C-P sphingoglycolipids isorated from Aplysia activated cAMP-dependent protein kinase by binding to the catalytic subunit of the enzyme. (theme 4) Genes of phosphoenolpyruvic acid (PnPy) phosphomutase and PnPy decarboxylase which were key enzymes for the synthesis of fosfomycin were cloned and a gene of p-methylating enzyme for the synthesis of C-P-C bond of bialaphos was cloned. (Theme 5) Oxygen of hemiacetal ring of sugar was replaced by phosphorus by sophisticated methods and many novel C-P compounds were chemically synthesized. Some of them were biologically active.

  • Research Products

    (34 results)

All Other

All Publications (34 results)

  • [Publications] Shigeko Araki: "Characterization of two novel pyruvylated glycosphingolipids containing 2'-aminoethylphosphoryl(→6)-galactose from the nervous system of Aplysia kurodai." J.Biochem.112. 461-469 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Toshiko Matsubara: "Occurrence of phosphonotetraglycosyl ceramide in the sea hare Dolabella auricularia." Biochim.Biophys.Acta. 1166. 55-63 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yoshihiro Yamaguchi: "Studies on the chemical structure of neutral glycosphingolipids in eggs of the sea hare,Aplysia juliana." Biochim.Biophys.Acta. 1165. 110-118 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yoshihiro Yamaguchi: "Structural elucidation of a novel phosphonoglycosphingolipid in eggs of the sea hare Aplysia juliana." Biochim.Biophys.Acta. 1165. 160-166 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Mitsuji Yamashita: "Novel synthesis of 2-phosphinoylphospholane 1-oxide derivatives." Bull.Chem.Soc.Jpn.65. 2004-2006 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Mitsuji Yamashita: "Preparation and structure of phosphono sugar N-glycosides." Chem.Lett.407-410 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sachiko Abe: "A new family of C-P glycosphingolipids in Aplysia:Structures and functions." Glycoconjugate J.10. 273-273 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Taro Hori: "Sphingolipids in lower animals." Prog.Lipid Res.32. 25-45 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Mutsumi Sugita: "Production of polyclonal antibody specific for mannose-containing tryglycosyl ceramide(Amino-CTH)and immuno-chemical detection of its hapten in crustacean." J.Jpn.Oil Chem.Soc.42. 649-655 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tomohisa Kuzuyama: "Studies on the biosynthesis of fosfomycin.V.Cloning of genes for fosfomycin biosynthesis." J.Antibiotics. 46. 1478-1480 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Mitsuji Yamashita: "Novel stereoselective preparation and conformational analysis of furanose-type phosphono sugar C-glycosides." Chem.Lett.93-96 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Mitsuji Yamashita: "Preparation of a novel non-natural phosphono sugar nucleoside derivative." Phosphorus.Sulfur.Silicon. 79. 293-296 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Mitsuji Yamashita: "Preparation of novel cyclophosphamide derivatives of sugar." Heterocycles. 36. 651-654 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Mitsuji Yamashita: "Reactions of 2-phospholene 1-oxides with bromine in some media:Facile preparation of bromohydrin derivatives of 2-phospholenes." Heteroatom Chem.4. 553-557 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Futoshi Arakane: "Glycolipids isolated from Aplysia kurodai can activate cyclic adenosine 3',5'-monophosphate-dependent protein kinase from rat brain." J.Neurochem.62. 86-93 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Mitsuji Yamashita: "X-ray crystallographic analysis of phosphono sugar and a novel preparation of phosphono sugar nucleoside derivatives." Chem.Lett.23-26 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Mitsuji Yamashita: "Novel efficient synthesis and structural analysis of furanose-type phosphono sugars." Heterocycles. 37(in press). (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Shigeko Araki et al.: "Characterization of two novel Pyruvylated glycosphingolipids containing 2'-aminoethylphosphorly (-6)-galactose from the nervous system of Aplysia Kurodai." J.Biochem.112. 461-469 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Toshiko Matsubara et al.: "Occurrence of phosphonotetraglycosyl ceramide in the sea hare Dolabella auricularia." Biochem.Biophys.Acta. 1166. 55-63 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshihoro Yamaguchi et al.: "Studies on the chemical structure of neutral glycosphingolipids in eggs of the sea hare, Aplysia juliana." Biochem.Biophys.Acta. 1165. 110-118 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshihiro Yamaguchi et al.: "Structural elucidation of a novel phosphonoglycosphingolipid in eggs of the sea hare Aplysia juliana." Biochem.Biophys.Acta. 1165. 160-166 (1192)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Mitsuji Yamashita et al.: "Novel synthesis of 2-phosphinoylphospholane 1-oxide derivatives." Bull.Chem.Soc.Jpn.65. 2004-2006 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Mitsuji Tamashita et al.: "Preparation and structure of phosphono sugar N-glycosides." Chem.Lett.407-410 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sachiko Abe et al.: "A new family of C-P glycosphingolipids in Aplysia : Structures and functions." Glycoconjugate J.10. 273-273 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Taro Hori et al.: "Sphingolipids in lower animals." Prog.Lipid Res.32. 25-45 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Mutsumi Sugita et al.: "Production of polyclonal antibody specific for mannose-containing tryglycosyl ceramide (Amino-CTH) and immunochemical detection of its hapten in crustacean." J.Jpn.Oil Chem.Soc.42. 649-655 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tomohisa Kuzuyama et al.: "Studies on the biosynthesis of fosfomycin. V.cloning of genes for fosfomysin biosynthesis." J.Antibiotics. 46. 1478-1480 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Mitsuji Tamashita et al.: "Novel stereo-selective preparation and conformational analysis of furanose-type phosphono sugar C-glycosides." Chem.Lett.93-96 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Mitsuji Yamashita et al.: "Preparation of a novel non-natural phosphono sugar nucleoside derivative." Phosphorus.Sulfur.Silicon. 79. 293-296 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Mitsuji Yamashita et al.: "Preparation of novel cyclophosphamide derivatives of sugar." Heterocycles. 36. 651-654 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Mitsuji Tamashita et al.: "Reactions of 2-phospholene 1-oxides with bromine in some media : Facile preparation of bromohydrin derivatives of 2-phospholenes." Heteroatom Chem.4. 553-557 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Futoshi Arakane et al.: "Glycolipids isolated from Aplysia Kurodai can activate cyclic adenosine 3', 5'-monophosphate-dependent protein kinase from rat brain." J.Neurochem.62. 86-93 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Mitsuji Yamashita et al.: "X-ray crystallographic analysis of phosphono sugar and a novel preparation of phosphono sugar nucleoside derivatives." Chem.Lett.23-26 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Mitsuji Yamashita et al.: "Novel efficient sysnthesis and structural analysis of furanose-type phosphono sugars." Heterocycles. 37. (in press) (1994)

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

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Published: 1995-03-27  

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