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Construction of peptides having molecular recognition ability by using novel α, α-disubstituted glycines

Research Project

Project/Area Number 11640552
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionKonan University

Principal Investigator

YAMADA Takashi  Konan Univ., Faculty of Science, Professor, 理学部, 教授 (00068123)

Co-Investigator(Kenkyū-buntansha) YANAGIHARA Ryoji  Konan Univ., Faculty of Science, Lecturer, 理学部, 講師 (50278793)
Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2000: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1999: ¥2,500,000 (Direct Cost: ¥2,500,000)
Keywordsα, α-disubstituted glycines / α, α-diphenylglycine / aminofluorene-carboxylic acid / α, α-di (2-pyridyl) glycine / X-ray structural analysis / conformation / complex formation / functional peptides / Ugi反応 / 蛍光スペクトル
Research Abstract

In this research project, we have intended to develop new functional peptides containing α, α-disubstituted glycines as key components. Because the side chains of α, α-disubstituted glycines are very crowded, they restrict the conformational mobility of peptide backbones and thus, stabilize the preferred conformation of the peptides. We investigated synthesis, conformation and intermolecular interaction of various peptides containing α-aminoisobutyric acid (Aib), α, α-diphenylglycine (Dph), 9-amino-fluorene-9-carboxylic acid (Afc) and α, α-di (2-pyridyl)glycine (2Dpy).
1.Tetrapeptides (Trp-Aib-Gly-Leu-NHAr) were synthesized, and were clarified to adopt β-turn stabilized by intramolecular hydrogen bonding and steric effect of Aib. The tetrapeptides bound quaternary ammonium salts as guests on the binding site composed of aromatic moieties at both terminals of the peptide, affording the 1 : 1 complex.
2.Pentapeptides (Z-AA_1-AA_1-Dph-AA_3-AA_3-OMe) and hexapeptides (Z-AA_1-Dph-AA_3-AA_1-Dp … More h-AA_3-OMe) containing α, α-diphenylglycine (Dph) were synthesized. By the X-ray structural analysis and NMR analysis, the pentapeptides where AA_1=Aib, were revealed to adopt 3_<10>-helix, whether AA_3 is Gly or Aib. Hexapeptide formed the 1 : 1 complex with dodecyl pyridinium salt.
3.Tripeptides (Z-AA_1-Afc-AA_3-OMe) and hexapeptides (Z-AA_1-Afc-AA_3-AA_1-Afc-AA_3-OMe) containing a novel α, α-disubstituted glycine, 9-aminofluorene-9-carboxylic acid (Afc), were synthesized using the Ugi reaction. Some hexapeptides also bound dodecyl pyridinium salt to make the 1 : 1 complex.
4.We succeeded in the first synthesis of tripeptides (Z-AA_1-2Dpy-AA_3-OMe) containing α, α-di (2-pyridyl)glycine (2Dpy). These tripeptides adopt a novel conformation in which each nitrogen atom of two pyridine rings forms an intramolecular hydrogen bond with hydrogen atoms of two amides, respectively. Furthermore, the tripeptides afforded crystals of the 2 : 1 complex with Cu ion, and the crystal structure were clarified by X-ray analysis. Less

Report

(3 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • Research Products

    (45 results)

All Other

All Publications (45 results)

  • [Publications] A.Lombardi: "The crystal structure of Afc-containing peptides"Biopolymers. 53. 150-160 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] V.Pavone: "Conformational behaivior of Cα,α-diphenyl glycine : Extended conformation in tripeptides containing consecutive Dφg residues"Biopolymers. 53. 161-168 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] G.De Simone: "The crystal structure of a Dcp-containing peptides"Biopolymers. 53. 182-188 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] R.Yanagihara: "Recognition of quarternary ammonium salts with tetrapeptides containing α-aminoisobutyric acid as a conformational constraint"J.Chem.Sac.,Perkin Trans.2. 551-556 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Synthesis of oligopeptides containing α,α-diphenylglycine"Peptide Science 1999. 143-146 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Facile synthesis of optically active a-methyl-α-amino acids"Peptide Science 1999. 147-150 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Fluorescence behavior of peptides containing 9-aminofluorene-9-carboxylic acid"Peptide Science 1999. 259-262 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Synthesis and conformation of tripeptides containing α,α-di(2-pyridyl)glycine"Peptide Science 1999. 303-306 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Synthesis and receptor-binding activity of endomorphin analogs containing α,α-disubstituted glycine"Peptide Science 1999. 441-444 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Synthesis of peptides containing a new metal-binding amino acid"Proc.Japanese-German Symp.on Peptide Science. 56-59 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Conformations and metal-complex formation of tripeptides containing α,α-disubstituted glycine with pyridin rings"Peptide Science 2000. 305-308 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Fluorescence behavior of very crowded tripeptides containing 9-aminofluorene-9-carboxylic acid"Peptide Science 2000. 417-424 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Study of the enzymatic degradation of endomorphin analogs containing α,α-disubstituted glycine"Peptide Science 2000. 421-424 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] A.Lombardi: "The crystal structure of Afc-containing peptides"Biopolymers. 53. 150-160 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] V.Pavone: "Conformational behaivior of Cα, α-diphenyl glycine : Extended conformation in tripeptides containing consecutive Dφg residues"Biopolymers. 53. 161-168 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] G.De Simone: "The crystal structure of a Dcp-containing peptides"Biopolymers. 53. 182-188 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] R.Yanagihara: "Recognition of quarternary ammonium salts with tetrapeptides containing α-aminoisobutyric acid as a confoemational constraint"J.Chem.Soc., Perkin Trans.. 2. 551-556 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Synthesis of oligopeptides containing α, α-diphenyl-glycine"Peptide Science 1999. 143-146 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Facile synthesis of optically active α-methyl-α-amino acids"Peptide Science 1999. 147-150 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Fluorescence behavior of peptides containing 9-amino-fluorene-9-carboxylic acid"Peptide Science 1999. 259-262 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Synthesis and conformation of tripeptides containing α, α-di (2-pyridyl) glycine"Peptide Science 1999. 303-306 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Synthesis and receptor-binding activity of endomorphin analogs containing α, α-disubstituted glycine"Peptide Science 1999. 441-444 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Synthesis of peptides containing a new metal-binding amino acid"Proc. Japanese-German Symp. on Peptide Science. 56-59 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Conformations and metal-complex formation of tripeptides containing α, α-disubstituted glycine with pyridin rings"Peptide Science 2000. 305-308 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Fluorescence behavior of very crowded tripeptides containing 9-aminofluorene-9-carboxylic acid"Peptide Science 2000. 417-424 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamada: "Study of the enzymatic degradation of endomorphin analogs containing α, α-disubstituted glycine"Peptide Science 2000. 421-424 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] R.Yanagihara: "Recognition of quarternary ammonium salts with tetrapeptides containing α-aminoisobutyric acid as a conformational constraints"J.Chem.Soc.,Perkin Trans.2. 551-556 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Yamada: "Synthesis of oligopeptides containing α,α- diphenylglycine"Peptide Science 1999. 143-146 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Yamada: "Facile synthesis of optically active α-methyl-α-amino acids"Peptide Science 1999. 147-150 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Yamada: "Fluorescence behavior of peptides containing 9-aminofluorene-9-carboxylic acid"Peptide Science 1999. 259-262 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Yamada: "Synthesis and conformation of tripeptides containing α,α-di(2-pyridyl) glycine"Peptide Science 1999. 303-306 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Yamada: "Synthesis and receptor-binding activity of endomorphin analogs containing α,α-disubstituted glycine"Peptide Science 1999. 441-444 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Yamada: "Synthesis of peptides containing a new metal-binding amino acid"Proc.Japanese-German Symp.on Peptide Science. 56-59 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Yamada: "Conformations and metal-complex formation of tripeptides containing α,α-disubstituted glycine with pyridin rings"Peptide Science 2000. (in press). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Yamada: "Fluorescence behavior of very crowded tripeptides containing 9-aminofluorene-9-carboxylic acid"Peptide Science 2000. (in press). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Yamada: "Study of the enzymatic degradation of endomorphin analogs containing α,α-disubstituted glycine"Peptide Science 2000. (in press). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] A.Lombardi: "The Crystal Structure of Afc-Containing Peptides"Biopolymers. 53. 150-160 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] V.Pavone: "Conformational Behaivior of Cα,α-Diphenyl Glycine : Extended Conformation in Tripeptides Containing Consecutive Dφg Residues"Biopolymers. 53. 161-168 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] G.De Simone: "The Crystal Structure of a Dcp-Containing Peptides"Biopolymers. 53. 182-188 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] R.Yanagihara: "Recognition of quarternary ammonium salts with tetrapeptides containing α-aminoisobutyric acid as a conformational constraint"J.Chem.Soc.,Perkin Trans.2. (in press). (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Yamada: "Synthesis of oligopeptides containing α,α-diphenylglycine"Peptide Science 1999. (in press). (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Yamada: "Facile synthesis of optically active α-methyl-α-amino acids"Peptide Science 1999. (in press). (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Yamada: "Fluorescence behavior of peptides containing 9-aminofluorene-9-carboxylic acid"Peptide Science 1999. (in press). (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Yamada: "Synthesis and conformation of tripeptides containing α,α-di(2-pyridyl)glycine"Peptide Science 1999. (in press). (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Yamada: "Synthesis and receptor-binding activity of endomorphin analogs containing α,α-disubstituted glycine"Peptide Science 1999. (in press). (2000)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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