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Development of Solid Phase Synthesis on Gold Nanoparticles

Research Project

Project/Area Number 13640549
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionOkayama University of Science

Principal Investigator

YAMADA Haruo  Okayama University of Science, Department of Chemistry, Professor, 理学部, 教授 (10175664)

Project Period (FY) 2001 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2002: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsSolid Phase Synthesis / Gold-Nanoparticle / Self-Assembled Monolayer / Peptide Synthesis on Solid / TEM / NMR / Dispersion / Aggregation / ペプチド固相合成 / アルカンチオール / Fmocグリシン / IR
Research Abstract

Solid phase synthesis on the polystyrene resin is devoid of sufficient chemical reactivity to allow the preparation of the complex organic molecules. Au nanoparticles functionalized with self-assembled monolayers (SAMs) of organothiols are inherently nanoscopic entities that provide a scaffold for the attachment of organic molecules, offering another environment for solid phase synthesis. To provide a nanoparticles for the solid phase synthesis, we prepared the various bifunctionalized alkanethiols. Reduction of HAuCl_4 with NaBH_4 in MeOH in the presence of the thiols resulted in the formation of Au nanoparticles coated with organic shells. The Au nanoparticles prepared are extremely stable and do not show any signs of decomposition. After purification of the nanoparticles via precipitation, Au nanoparticles can be characterized by NMR and IR. High resolution TEM photographs of the nanoparticles showed that they have diameters in the range of 1 - 4 nm and an average in the particle size distribution at 2.8 nm. Loading amount of the thiols are determined by treatment of the Au nanoparticles with I_2, which liberate organic substrates as disulfides. The loading amounts are in the range of 1 - 4 mmol/g, depending on the thiols used.
Solid phase synthesis of peptides on the Au nanoparticles is examined. We prepared the Au nanoparticles coated with FmocGly. After deprotection of Fmoc group, coupling of Fmoc protected amino acids gave the depeptides.

Report

(3 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • Research Products

    (19 results)

All Other

All Publications (19 results)

  • [Publications] Hiroshi Tanaka: "Synthesis of Di-Branched Heptasaccharide by One-Pot Glycosylation Using Sevent Independent Buildinig Blocks"Organic Lett.. 4・24. 4213-4216 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Katsuya Matsui: "Stereoselective Synthesis fo the C(1)-C(12) Fragments of Tedanolides -Application of a syn-Selectice Tin(II)-Mediated Aldol Reaction and a Convertible Methoxybenzyl"Eur. J. Org. Chem.. 3615-3624 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Kazuoki Nakai: "Stereo-and Regio-selective Ti-mediated Radical Cyclization of Epoxy-alkanes : Synthesis of the A and C ring synthons of paclitaxel"Tetrahedron Lett.. 42・44. 7855-7857 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Haruo Yamada: "Mixed Branched-Linear Type One-Pot Glycosylation : Synthesis of Hepta b-D-Glucoside"Synlett.. 11. 1751-1754 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Haruo Yamada: "Total Synthesis of Smenospondiol by Ti-mediated Tandem Radical Cyclization"Synlett.. 12. 1935-1937 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hiroshi Tanaka., Masaatsu Adachi., Hirokazu Tsukamoto., Takeji Ikeda., Haruo Yamada., Takashi Takahashi.: "Synthesis of Di-Branched Heptasaccharide by One-Pot Glycosylation Using Sevent Independent Building Blocks"Organic Lett.. 4(24). 4213-4216 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Katsuya Matsui., Bao-Zhong Zheng., Shinichi Kusaka., Masaya Kuroda., Katsuya Yoshimura., Haruo Yamada., Osamu Yonemitsu.: "Stereoselective Synthesis of the C(1)-C(12) Fragments of Tedanolides - Application of a syn-Selectice Tin(II)-Mediated Aldol Reaction and a Convertible Methoxybenzyl protecting Group"Eur. J. Org. Chem.. 3615-3624 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Kazuoki Nakai., Miyuki Kamoshita., Takayuki Doi., Haruo Yamada., Takashi Takahashi.: "Stereo- and Regio-selective Ti-mediated Radical Cyclization of Epoxy-alkanes: Synthesis of the A and Cring synthons of paclitaxel"Tetrahedron Lett.. 42(44). 7855-7857 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Haruo Yamada., Hisami Takimoto., Takeji Ikeda., Hirokazu Tsumoto., Takeo Harada., Takashi Takahashi.: "Mixed Branched-Linear Type One-Pot Glycosylation: Synthesis of Hepta β-D-Glucoside"Synlett.. 11. 1751-1754 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Haruo Yamada., Tsuyoshi Hasegawa., Hiroshi Tanaka., Takashi Takahashi.: "Total Synthesis of Smenospondiol by Ti-mediated Tandem Radical Cyclization"Synlett.. 12. 1935-1937

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hiroshi Tanaka: "Synthesis of Di-Branched Heptasaccharide by One-Pot Glycosylation Using Seven Independent Building Blocks"Organic Lett.. 4・24. 4213-4216 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Kazuhiko Nakai: "Stereo-and Regio-selective Ti-mediated Radical Cyclization of Epoxyalkanes: Synthesis of the A and C ring synthons of paclitaxel"Tetrahedron Lett.. 42・44. 7855-7857 (2001)

    • Related Report
      2002 Annual Research Report
  • [Publications] Katsuya Matsui: "Stereoselective Synthesis of the C(1)-C(12) Fragments of Tedanolides-Application of a syn-Selectice Tin(II)-Mediated Aldol Reaction"Eur. J. Org. Chem.. 3615-3624 (2001)

    • Related Report
      2002 Annual Research Report
  • [Publications] Haruo Yamada: "Mixed Branched-Linear Type One-Pot Glycosylation: Synthesis of Hepta β-D-Glucoside"Synlett. 11. 1751-1754 (2001)

    • Related Report
      2002 Annual Research Report
  • [Publications] Haruo Yamada: "Total Synthesis of Smenospondiol by Ti-mediated Tandem Radical Cyclization"Synlett. 12. 1935-1937 (2001)

    • Related Report
      2002 Annual Research Report
  • [Publications] Katsuya Matsui: "Stereoselective Synthesis of the C(1)-C(12) Fragments of Tedanolides-Application of a syn-Selectice Tin(II)-Mediated Aldol Reaction and a Convertible Methoxybenzyl Protecting Group"Eur. J. Org. Chem.. 3615-3624 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Kazuhiko Nakai: "Stereo-and Regio-selective Ti-mediated Radical Cyclization of Epoxy-alkanes : Synthesis of the A and C ring synthons of paclitaxel"Tetrahedron Lett.. 42, 44. 7855-7857 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Haruo Yamada: "Mixed Branched-Linear Type One-Pot Glycosylation : Synthesis of Hepta b-D-Glucoside"Synlett. 11. 1751-1754 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Haruo Yamada: "Total Synthesis of Smenospondiol by Ti-mediated Tandem Radical Cyclization"Synlett. 12. 1935-1937 (2001)

    • Related Report
      2001 Annual Research Report

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

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