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Preparation of Anti-Ciguatoxin Antibody and Synthetic Study of Ciguatoxin Science

Research Project

Project/Area Number 09640621
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

OISHI Toru  Chemistry, Tohoku Univ., Lecturer, 大学院・理学研究科, 講師 (90241520)

Project Period (FY) 1997 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 1999: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1998: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1997: ¥1,300,000 (Direct Cost: ¥1,300,000)
Keywordsciguatoxin / polycyclicether / seafood poisoning / anti-ciguatoxin antibody / total synthesis / convergent synthesis / olefin metathesis
Research Abstract

Ciguatera is a widespread human food poisoning that is caused by fishes dwelling in coral reefs in the tropics and subtropics. Over twenty thousands people in subtropical and tropical regions suffered annually from ciguatera caused by poisonous fishes dwelling in coral reefs. Ciguatoxin is the principal toxin of ciguatera, and we determined the absolute configuration by CD exciton chirality method. Considerable attention has been paid to develop an analyzing method for detecting the toxic fishes, because the prevalence of ciguatera has threatened public health in tropical regions. Therefore, anti-ciguatoxin antibody is needed for this purpose. We succeeded in the preparation of anti-ciguatoxin antibody using AB-ring protein conjugates as haptens. Synthesis of ciguatoxin has received considerable attention among synthetic chemists due to the striking feature and biological features of these toxins. We developed a new method useful for constructing polycyclic ether systems using alkylation and ring-closing metathesis reaction. Based on this strategy, we successfully synthesized the ABCED ring fragment starting with the AB and E ring, respectively. Alternatively, we synthesized the IJKLM ring fragment via Tebbe reagent mediated ring-closing metathesis, and the chemo- and stereoselective reduction of the methyl acetal. Studies toward total synthesis of ciguatoxin are currently underway.

Report

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

    (31 results)

All Other

All Publications (31 results)

  • [Publications] Tohru Oishi: "Enantioselective Synthesis of Medium Ring Ethers, Tetrahydrooxepin, Oxocane and Hexahydrooxonin, of Ciguatoxin Extensive Ring-Expansion and Chemoenzymatic"Tetrahedron. 55. 7471-7498 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Hiroki Oguri: "Expeditious Tandem-Metathesis Route to the AB-ring Fragment of Ciguatoxin"Tetrahedron Letters. 40. 5405-5408 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Kenji Maeda: "Convergent Synthesis of the ABCDE Ring Framework of Ciguatoxin"Chemical Communications. 1063-1064 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Hiroki Oguri: "Designed Hapten Aimed at Anti-Ciguatoxin Monoclonal antibody : Synthesis Immunization and Discrimination of the C2 Configuration"Synthesis. 1431-1436 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Hisatoshi Uehara: "The Absolute Configuration and Total Synthesis of Korormicin"Tetrahedron Letters. 40. 8641-8645 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Tohru Oishi: "Convergent Synthesis of the IJKLM Ring Fragment of Ciguatoxin CTX3C"Chemical Communications. 2035-2036 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Hiroki Oguri, Shojiro Hishiyama, Ohki Sato, Tohru Oishi, Masahiro Hirama, Michio Murata, Takeshi Yasumoto, and Nobuyuki Harada: "Synthetic Study of Ciguatoxin. Absolute Configuration of the C2 Hydroxy Group"Tetrahedron. 53. 3057-3072 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Tohru Oishi, Kenji Maeda, and Masahiro Hirama: "Stereocontrolled Synthesis of the HIJ Ring System of Ciguatoxin"Chem. Commun.. 1289-1290 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Tohru Oishi, Yoko Nagumo, and Masahiro Hirama: "Convergent Synthesis of a Trans-fused 6-7-6 Tricyclic Ether System Based on a Ring-closing Metathesis Reaction"Synlett. 980-982 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Tohru Oishi, Mitsuru Shoji, Naomi Kumahara, and Masahiro Hirama: "Stereoselective Synthesis of the LM Ring Moiety of Ciguatoxin : Reagent Control of Asymmetric Dihydroxylation"Chem. Lett.. 845-846 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Masayuki Satake, Akio Morohashi, Hiroki Oguri, Tohru Oishi, Masahiro Hirama, Nobuyuki Harada, and Takeshi Yasumoto: "The Absolute Configuration of Ciguatoxin"J. Am. Chem. Soc.. 118. 11325-11326 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Tohru Oishi, Yoko Nagumo, and Masahiro Hirama: "Convergent Synthesis of the Trans-fused 6-n-6-6 (n=7-10) Tetracyclic Ether System Based on a Ring-closing Metathesis Reaction"Chem. Commun.. 1041-1042 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Tohru Oishi, Megumi Maruyama, Kenji Maeda, Mitsuru Shoji, Shin-ichiro Tanaka, and Masahiro Hirama: "Enantioselective Synthesis of the Medium Ring Ethers, Tetrahydrooxepin, Oxocane, and Hexahydrooxonin, of Ciguatoxin. Extensive Ring-Expansion and Chemoenzymatic Desymmetrization Strategy"Tetrahedron. 55. 7472-7498 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Kenji Maeda, Tohru Oishi, Hiroki Oguri, and Masahiro Hirama: "Convergent Synthesis of the ABCDE Ring Fragment of Ciguatoxin"Chem. Comun.. 1063-1064 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Hiroki Oguri, Shin-ya, Sasaki, Tohru Oishi, and Masahiro hirama: "Expeditious Tandem-Metathesis Route to the AB-ring Fragment of Ciguatoxin"Tetrahedron Lett.. 40. 5405-5408 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Hiroki Oguri, Shin-ichiro Tanaka, Shojiro Hishiyama, Tohru Oishi, Masahiro Hirama, Takeshi Tumuraya, Yoshihisa Tomioka, and Michinao Mizugaki: "Designed Hapten Aimed at Anti-Ciguatoxin Antibody : Synthesis, Immunization and Discrimination of the C2 Configuration"Synthesis. 1431-1436 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Tohru Oishi, Yoko Nagumo, Mitsuru Shoji, Jean-Yves Le Brazidec, Hisatoshi Uehara and Masahiro Hirama: "Convergent Synthesis of the IJKLM Ring Fragment of Ciguatoxin CTX3C"Chem. Commun.. 2035-2036 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Hisatoshi Uehara, Tohru Oishi, Kazuhiro Yoshikawa, Kenichi Mochida, and Masahiro Hirama: "The Absolute Configuration and Total Synthesis of Korormicin"Tetrahedron Lett.. 40. 8641-8645 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Tohru Oishi: "Enantioselective Synthesis of the Medium Ring Ethers, Tetrahydrooxepin Oxocane and Hexahydrooxonin, of Ciguatoxin. Extensive Ring-Expansion"Tetrahedron. 55・24. 7471-7498 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hiroki Oguri: "Expeditious Tandem-Metathesis Route to the AB-ring Fragment of Ciguatoxin"Tetrahedron Letters. 40・29. 5405-5408 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Kenji Maeda: "Convergent Synthesis of the ABCDE Ring Framework of Ciguatoxin"Chemical Communications. -・12. 1063-1064 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hiroki Oguri: "Designed Hapten Aimed at Anti-Ciguatoxin Monoclonal Antibody : Synthesis, Immunization and Discrimination of the C2 Configuration"Synthesis. -・special. 1431-1436 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hisatoshi Uehara: "The Absolute Configuration and Total Synthesis of Korormicin"Tetrahedron Letters. 40・49. 8641-8645 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Tohru Oishi: "Convergent Synthesis of the IJKLM Ring Fragment of Ciguatoxin CTX3C"Chemical Communications. -・20. 2035-2036 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Tohru Oishi: "Convergent synthesis of the trans-fused 6-n-6-6 (n=7-10) tetracyclic ethersystem based on a ring-closing metathesis reaction" Chem.Commun.1041-1042 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hiroki Oguri: "Designed hopten aimed at anti-ciguatoxin monoclonal antibody : Synthesis,Immunization and discrimination of the C2 configuration" Synthesis. in press. (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Masayuki Satake: "The absolute cofiguration of ciguatoxin" J.Am.Chem.Soc.119・46. 11325-11326 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Tohru Oishi: "Stereoselective synthesis of the LM ring moiety of Ciguatoxin" Chem.Lett.845-846 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Tohru Oishi: "Convergent synthesis of a trans-fused 6-7-6 tricyclic ether system" Synlett. 980-982 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Tohru Oishi: "Stereocontrolled synthesis of the HIJ ring system of ciguatoxin" Chem.Commun.1289-1290 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Hiroki Oguri: "Synthetic study of ciguatoxin Absolute configuration of the C2 hydroxy group" Tetra hedron. 53・9. 3057-3072 (1997)

    • Related Report
      1997 Annual Research Report

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

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