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The First Total Synthesis of Various Thiostrepton-type Macrocyclic Antibiotics and the Structure-Bioactivity Relationship.

Research Project

Project/Area Number 14550829
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKanagawa University

Principal Investigator

SHIN Chung-gi  SHIN,Chung-gi, 工学部, 教授 (20078306)

Co-Investigator(Kenkyū-buntansha) YONEZAWA Yasuchika  Kanagawa University, Applied Chemistry, Assistant, 工学部, 助手 (70078335)
Project Period (FY) 2002 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2003: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2002: ¥2,700,000 (Direct Cost: ¥2,700,000)
KeywordsThiostrepton antibiotics / Thiocillins I / Sulfomycins / Cyclochiazomycin / Dehydrooligopeptide / Total synthesis / 2,3,5-Tristhiazolyl pyridine. / Dehydrothiazole amino acid. / Dehydrooxazole amino acid. / ビストラタミド / スロホマイシン / ベルニナマイシン / テロメスタチン
Research Abstract

Recently, many thiostrepton-type macrocyclic antibiotics, such as micrococcin P and P_1, and GE 2270 A, have been isolated from various secondary metabolites of Buchillus pumilus and Planobispola rose, respectively. The natural products exhibit very interesting bioactivities, such as antitumor and antibacterial activities, and include a characteristic main structure, in common 2,3,6-tristhiazolyl-substituted pyridine skeleton called Fragment A-C constructed of a polythiazole pyridine segment [Fragment A] and thiazolyl side chain called Fragment C. Furthermore, a unique polysubstitutedthiazole segment called Fragment B as a substructure. The total syntheses of the above mentioned antibiotics have been already accomplished by us. Here, similarly to the cases of the micrococcins P, P_1 and GE 2270 A, the first total synthesis of thiocilline I and convenient synthesis of the Fragment B-C of sulfomycin I, isolated from Bucillus bodius and Streptomyces viridchromogenes MCRL-0368 respectively, have been also achieved, after syntheses of he each Fragments A, B, and C, and then fragment condensations. These results will certainly contribute to the total synthesis of other similar thiostrepton-type antibiotics.

Report

(3 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • Research Products

    (25 results)

All Other

All Publications (25 results)

  • [Publications] C.Shin, Y.Yonezawa, et al.: "Convenient Synthesis of the Main Tridehydropentapeptide Skeleto for a Macrocyclic Antibiotic, Sulfomycin I."Chem.Lett.. 33. 72-73 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] C.Shin, Y.Yonezawa, et al.: "Useful Synthesis of the Main Central 2,3,6-Trisubstituted Pyridine Skeleton of Various Thiostrepton-type Macrocyclic Antibiotics."Heterocycles. 61. 45-50 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] C.Shin, Y.Yonezawa, et al.: "Useful Synthesis of the Longer Array Oxazole Rings for Telomestatin."Heterocycles. 60. 1567-1572 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Yonezawa, C.Shin, et al.: "Novel Synthesis of 5-Oxomorpholine Derivative by Intramolecular Cyclization."Heterocycles. 60. 1377-1385 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] C.Shin, Y.Yonezawa, et al.: "Useful Synthesis of Various Thiazole and Polythiazolyl Derivatives from Thiocarboxamide and β-Bromoacyl Compound."Heterocycles. 60. 321-335 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] C.Shin, Y.Yonezawa, et al.: "Asymmetric Synthesis of the Main Pyridine Skeleton Constructing a Macrocyclic Antibiotic, Cyclothiazomycin."Bull.Chem.Soc.Jpn.. 76. 643-644 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 辛 重基(分担執筆): "プロティンエンジニアリングの基礎(普及版)"シーエムシー. 350 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kayano, Y.Yonezawa, C.Shin: "Convenient Synthesis of the Main Tridehydropentapeptide Skeleton for a Macrocyclic Antibiotic, Sulfomycin I"Chem.Lett.. 33. 72-73 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] C.Shin, H.Saito, Y.Yonezawa: "Useful Synthesis of the Main Central 2,3,5-Trisubstituted Pyridine Skeleton of Various Thiostrepton-type Macrocyclic Antibiotics"Heterocycles. 61. 45-50 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Endoh, K.Tsuboi, R.Kim, Y.Yasuchika, C.Shin: "Useful Synthesis of the Longer Array Oxazole Rings for Telomestatin"Heterocycles. 60. 1567-1572 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] D.Yoshioka, K.Inoue, Y.Yonezawa, C.Shin: "Novel Synthesis of 5-Oxomorpholine Derivative by Cyclization of Δ^1-Dehydrodipeptide"Heterocycles. 60. 1377-1385 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Endoh, Y.Yonezawa, C.Shin: "Asymmetric Synthesis of the Main Pyridine Skeleton for a Macrobicyclic Antibiotic, Cyclothiazomycin"Bull.Chem.Soc.Jpn.. 76. 643-644 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] A.Nagasaki, Y.Adachi, Y.Yonezawa, C.Shin: "Useful Synthesis of Various Thiazole and Polythiazolyl Derivatives from Thiocarboxamide and β-Bromoacyl Compound"Heterocycles. 60. 321-335 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 辛重基: "プロテインエンジニアリングの基礎[普及版]"シーエムシー. 138-152 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] C.Shin, Y.Yonezawa, et al.: "Convenient Synthesis of the Main Tridehydropentapeptide Skeleton for a Macrocyclic Antibiotic, Sulfomycin I."Chem.Lett.. 33. 72-73 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] C.Shin, Y.Yonezawa, et al.: "Useful Synthesis of the Main Central 2,3,6-Trisubstituted Pyridine Skeleton of Various Thiostrepton-type Macrocyclic Antibiotics."Heterocycles. 61. 45-50 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] C.Shin, Y.Yonezawa, et al.: "Useful Synthesis of the Longer Array Oxazole Rings for Telomestatin."Heterocycles. 60. 1567-1572 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Y.Yonezawa, C.Shin, et al.: "Novel Synthesis of 5-Oxomorpholine Derivative by Intramolecular Cyclization."Heterocycles. 60. 1377-1385 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] C.Shin, Y.Yonezawa, et al.: "Useful Synthesis of Various Thiazole and Polythiazolyl Derivatives from Thiocarboxamide and β-Bromoacyl Compound."Heterocycles. 60. 321-335 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] C.Shin, Y.Yonezawa, et al.: "Asymmetric Synthesis of the Main Pyridine Skeleton Constructing a Macrocyclic Antibiotic, Cyclothiazomycin."Bull.Chem.Soc.Jpn.. 76. 643-644 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 辛 重基(分担執筆): "プロティンエンジニアリングの基礎 (普及版)"シーエムシー. 350 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] E.Endo, C.Shin, et al.: "Asynmmetric Synthesis of the Main Skeleton for a Macrobiocyclic Antibiotic, Cyclothiazomycin"Bull. Chem, Soc, Jpn.. (in press). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] C.Shin, Y.Yonezawa, et al.: "Convenient Synthesis of the Main Dehydrohexapeptide Skeleton Constituting a Macrocyclic Antibiotic, Berninamycin A"Chem. Lett.. 1098-1099 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] C.Shin, Y.Yonezawa, et al.: "Novel Synthesis of the Main Central 2,3,6-Trisubstituted Pyridine Skeleton [Fragment A-B-C] of a Macrobicyclic Antibiotic, Cyclo-thiazomycin"Bull.Chem.Soc.Jpn.. 75. 1583-1596 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Y.Yonezawa, C.Shin, et al.: "A Synthesis of a Hydroxyvaline-derived Thiazole-4-carboxylate Constituting an Antibiotic, Thiocilline I."Heterocycles. 57. 903-908 (2002)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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