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New method for organic synthesis based on affinity separation

Research Project

Project/Area Number 12640571
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 物質変換
Research InstitutionOsaka University

Principal Investigator

FUKASE Koichi  Osaka University, Graduate School of Science, Associate Professor, 大学院・理学研究科, 助教授 (80192722)

Project Period (FY) 2000 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2001: ¥1,700,000 (Direct Cost: ¥1,700,000)
Fiscal Year 2000: ¥1,900,000 (Direct Cost: ¥1,900,000)
Keywordsaffinity separation / oligosaccharide / peptide / molecular recognition / high through put synthesis / glycoconjugate / lipid A / library / ピリドA / タグ / 固相合成
Research Abstract

A new method named synthesis based on affinity separation (SAS) was developed for high throughput synthesis : the reaction is carried out in solution and the desired products can be isolated rapidly by the host-guest interaction between the solid-support and the desired products which possess the host and guest structures, respectively.
The interaction between crown ether (32-crown-10) and ammonium ion was previously found to be useful for this purpose. The synthesis started with a starting material tagged with the crown ether. After each reaction cycle, the reaction mixture was applied to the aminomethylated polystyrene column (trifluoroacetic acid form). The compound possessing the crown ether was selectively adsorbed on the column, whereas other impurities without the crown ether such as excess reagents and byproducts were washed off. Subsequent desorption with CH_2CL_2-MeOH (1 : 1) afforded the desired compound in high yield. We then found Triton X-100 (polyethylene glycol based detergent) can be used as a tag in place of 32-crown-10.
The interaction between a barbituric acid derivative and its artificial receptor [= bis(2,6-diaminopyridine)amide of isophthalic acid] was also found to be effective. Both methods were applied to the synthesis of peptides, heterocycles, and oligosaccharides. New efficient synthesis of lipid A, an immunostimulating glycoconjugate of bacteria, was achieved by using the latter method. The small lipid A library was also constructed by the method. These new strategies are expected to be useful for, particularly, multiple parallel synthesis and combinatorial library preparation.

Report

(3 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • Research Products

    (14 results)

All Other

All Publications (14 results)

  • [Publications] San-Qi Zhang: "Synthesis based on affinity separation (SAS) : seaparation of products having barbituric acid tag from untagged compounds by using hydrogen boud interaction"Synlett. 5. 590-596 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Yoshiyuki Fukas: "New Efficient Route for Synthesis of Lipid A by Using Affinity Separation"Synlett. 10. 1693-1698 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 深瀬 浩一: "効率的な糖鎖合成を目指して"有機合成化学協会誌. 59\5. 98-99 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 深瀬 浩一: "生命化学のニューセントラルドグマ"化学同人. 8 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 深瀬 浩一: "コンビナトリアルサイェンスの新展開"シーエムシー出版. 13 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Yoshiyuki Fukase, San-Qi Zhang, Keiko Iseki, Masato Oikawa, Koichi Fukase, Shoichi Kusumoto: "New Efficient Route for Synthesis of Lipid A by Using Affinity Separation"Synlett. 1693 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Kenji Egusa, Shoichi Kusumoto, Koichi Fukase: "A new catch-and-release purification method using a 4-azido-3-chlorobenzyl group"Synlett. 777 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] San-Qi Zhang, Koichi Fukase, Minoru Izumi, Yoshiyuki Fukase, Shoichi Kusumoto: "Synthesis based on affinity separation (SAS) : separation of products having barbituric acid tag from untagged compounds by using hydrogen bond interaction"Synlett. 590 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Koichi Fukase: "Combinatorial and Solid-Phase Methods in Oligosaccharide Synthesis"Glycoscience, Chemistry and Chemical Biology, ed. by B. Fraser-Reid, K. Tatsuta, J. Thiem, Springer. (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] San-Qi Zhang: "Synthesis based on affinity separation (SAS) : seaparation of products having barbituric aced tag from untagged compounds by using hydrogen bond interaction"Synlett. ・5. 590-596 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Yoshiyuki Fukase: "New Efficient route for Synthesis of Lipid A by Using Affinity Separation"Synlett. ・10. 1693-1698 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] 深瀬 浩一: "効率的な糖鎖合成を目指して"有機合成化学協会誌. 59・5. 98-99 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] 深瀬 浩一: "生命化学のニューセントラルドグマ"化学同人. 8 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] 深瀬 浩一: "コンビナトリアルサイエンスの新展開"シーエムシー出版. 13 (2002)

    • Related Report
      2001 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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