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Synthesis and Development of Useful Glycosidase Inhibitors.

Research Project

Project/Area Number 08455419
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field 有機工業化学
Research InstitutionWaseda University

Principal Investigator

TATSUTA Kuniaki  School of Sci.& Eng., Waseda University, Professor, 理工学部, 教授 (40051627)

Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥7,800,000 (Direct Cost: ¥7,800,000)
Fiscal Year 1997: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1996: ¥6,000,000 (Direct Cost: ¥6,000,000)
KeywordsEnzyme inhibitor / Natural product / Bioactive compounds / Total synthesis / Industrial / Carbohydrate / Heterocycle / Glycoscience / 酵素阻害 / 抗生物質
Research Abstract

In recent years, much attention has focused on the synthesis and development of glycosidase inhibitors because of an increasing awareness of the vital role playd by carbohydrates in biological processes. Therefore, the chemical and biochemical studies on glycosidase inhibitors may lead to understand the molecular basis of intractable diseases such as diabetes mellitus, cancer and AIDS,and may also provide us therapeutic approaches to them.
As part of an ongoing program to clarify the mode of action of glycosidase inhibitors, we have synthesized cyclophellitol, nagstatin and gualamycin, and their analogs having different configurations and functionalities.
Nagstatin is a natural inhibitor of N-acetyl-beta-D-glucosaminidase, and gualamycin is an antimite substance.
Herein, nagstatins including a variety of hydroxyl and triazole analogs have been synthesized from carbohydrates by inter-and intramolecular nucleophilic reaction of the imidazole and triazole moieties. Their glycosidase inhibiting activities were quite substrate-specific, indicating that the glycosidases recognize especially each carbons and configurations of the glycosidase inhibitors, and consequently, the inhibitors serve as antagonists of the corresponding glycopyranosides.
Total synthesis of gualamycin has been accomplished from three kinds of carbohydrates through glycosylation of a thio-phenol derivative of the disaccharide portion with a pyrrolidine-aglycone. The anti-mite activity of gualamycin was suggested to be due to its maltase inhibiting activity.

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • Research Products

    (23 results)

All Other

All Publications (23 results)

  • [Publications] Kuniaki Tatsuta: "The first total synthesis of calbistrin A,amicrobial product possessing multiple bioactivities" Tetrahedron Letters. 38・4. 583-586 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kuniaki Tatsuta: "Total synthesis of progesterone receptor ligands,(-)-PF1092A,B snd C." Tetrahedron Letters. 38・8. 1439-1442 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kuniaki Tatsuta,: "Total synthesis of MS-444,a myosin light chain kinasa inhibitor." Journal of Antibiotics. 50・3. 289-290 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kuniaki Tatsuta: "NK10958,a novel plant growth regulator produced by Steptomyces sp.." Journal of Antibiotics. 50・3. 259-260 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kuniaki Tatsuta,: "The total synthesis of a glycosidase inhibitor,nagstatin." Bulletin of the Chemical Society of Japan. 70・2. 427-436 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kuniaki Tatsuta,: "The first total synthesis of(±)-terpestacin,HIV syncytium formation inhibitor." Tetrahedron Letters. 39・1. 83-86 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kuniaki Tatsuta: "The first synthesis of calbistrin A,a microbial product possessing multiple bioactivities." Tetrahedron Lett.38. 583-586 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kuniaki Tatsuta: "Total synthesis of progesterone receptor ligands, (-) -PF1092A,B and C." Tetrahedron Lett.38. 1439-1442 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kuniaki Tatsuta: "Total synthesis of MS-444, a myosin light chain kinase inhibitor." J.Antibiot.50. 289-290 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kuniaki Tatsuta: "NK10958, a novel plant growth regulator produced by Streptomyces sp." J.Antibiot.50. 259-260 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kuniaki Tatsuta: "The total synthesis of a glycosidase inhibitor, nagstatin." Bull.Chem.Soc.Jpn.70. 427-436 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kuniaki Tatsuta: "The first total synthesis of ((]SY.+-。[)) -terpestacin, HIV syncytium formation inhibitor." Tetrahedron Lett.39. 83-86 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kuniaki Tatsuta: "The first total synthesis of calbistrin A, a microbial product possessing multiple bioactivities." Tetrahedron Letters. 38・4. 583-586 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Kuniaki Tatsuta: "Total synthesis of progesterone receptor ligands, (-)-PF1092A, B and C." Tetrahedron Letters. 38・8. 1439-1442 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Kuniaki Tatsuta: "Total synthesis of MS-444, a myosin light chain kinasa inhibitor." Journal of Antibiotics. 50・3. 289-290 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Kuniaki Tatsuta: "NK10958, a novel plant growth regulator produced by Steptomysces sp.." Journal of Antibiotics. 50・3. 259-260 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Kuniaki Tatsuta: "The total synthesis of a glycosidase inhibitor, nagstain." Bulletin of the Chemical Society of Japan. 70・2. 427-436 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Kuniaki Tatsuta: "The first total synthesis of (±)-terpestacin, HIV syncytium formation inhibitor." Tetrahedron Letters. 39・1. 83-86 (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Kuniaki Tatsuta: "Synthesis and Glycosidase Inhibitory Activities of Nagstatin Triazole Analogs." J.Antibit.49・8. 836-838 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kuniaki Tatsuta: "Total synthesis and chemical design of useful glycosidase inhibitors." Pure & Appl.Chem.68・6. 1341-1346 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kuniaki Tatsuta: "Total Synthesis of Deacetyl-caloporoside,a Novel Inhibitor of the GABAA Receptor Ion Channel." Tetrahedoron Lett.37・14. 2453-2456 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kuniaki Tatsuta: "Synthesis and Biological Evaluation of Caloporoside Analogs." J.Antibiot.49・7. 713-715 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kuniaki Tatsuta: "The First Toatl Synthesis of Calbistrin A,a Microbial Product Possessing Multiple Bioactivities." Tetrahedoron Lett.38・4. 583-586 (1997)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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