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2003 Fiscal Year Final Research Report Summary

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
KeywordsThiostrepton antibiotics / Thiocillins I / Sulfomycins / Cyclochiazomycin / Dehydrooligopeptide / Total synthesis / 2,3,5-Tristhiazolyl pyridine. / Dehydrothiazole amino acid. / Dehydrooxazole amino acid.
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.

  • Research Products

    (14 results)

All Other

All Publications (14 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 2005-04-19  

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