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Non-proteinogenic amino acids - asymmetric synthesis, secondary structure, and biological activity -

Research Project

Project/Area Number 13672219
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionKyushu University

Principal Investigator

TANAKA Masakazu  Kyushu University, Graduate School of pharmaceutical Sciences, Associate Professor, 大学院・薬学研究院, 助教授 (00227175)

Project Period (FY) 2001 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2002: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2001: ¥2,800,000 (Direct Cost: ¥2,800,000)
Keywordsα,α-disubstituted amino acids / helix / conformation / peptide / diethylglycine / Aib / X-ray crystallography / X線構造解析 / 光学活性環状アミノ酸 / X-線結晶解析 / α-エチル化アミノ酸 / アルキル化アミノ酸
Research Abstract

Optically active α,α-disubstituted amino acids were synthesized using (S,S)-cyclohexane-1,2-diol as a chiral auxiliary. Homo- and hetero-peptides containing α-ethylated α,α-disubstituted amino acid, αEtLeu in Aib and Deg sequences were prepared, and also heteropeptide constituted of diverse α-ethylated α,α-disubstituted amino acids was synthesized. The conformation of pentapeptides was studied by using CD, FT-IR, H NMR, and X-ray. In solution, the dominant conformation of heteropeptide Tfa-[(S)-αEtVal-(S)-αEtLeu-(S)-αEtNva-Deg-(S)-αEtNle]-OEt was a fully planar C_5-conformation, and those of the other peptides were 3_<10>-helical structures. In the crystalline state, all pentapeptides showed the 3_<10>-helical structures. Furthermore, we synthesized chiral cyclic α,α-disubstituted amino acids starting from dimethyl tartrate, and prepared its homo- and heteropeptides. The conformation of its peptides seem to be formed the 3_<10>-helical structure preferentially. The antibacterial activity of peptides was examined, but none of peptides showed strong activity.

Report

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

    (35 results)

All Other

All Publications (35 results)

  • [Publications] M.Tanaka: "Asymmetric Synthesis of α,α-Disubstituted α-Amino Acids Using (S, S)-Cyclohexane-1,2-diol as a Chiral Auxiliary"J.Org.Chem.. 66. 2667-2673 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Tanaka: "Solid-State Conformation of a Hybrid Tripeptide Between β-Amino Acid 8-Aminocyclooct-4-enecarboxylic Acid and 2-Aminoisobutyric Acid"Chem.Pharm.Bull.. 49. 1178-1181 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 田中正一: "α,α-ジ置換アミノ酸よりなるペプチドのコンフォメーションと分子設計"有機合成化学協会誌. 60. 125-136 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Tanaka: "Asymmetric Synthesis and Conformational Analysis of α,α-Disubstituted α-Amino Acids and Their Peptides"Peptide Science 2001. 263-266 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Kurihara: "Conformation of Oligopeptides Containing Chiral α,α-Disubstituted Amino Acids : Computational Study"Peptide Science 2001. 287-288 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Oba: "Conformation of Peptides Containing a Chiral α-Ethylated α,α-Disubstituted α-Amino Acid : (S)-αEthylleucine (=(2S)-2-Amino-2-ethyl-4-methylpentanoic Acid) within Sequences of Dimethylglycine and Diethylglycine Residues"Helvetica Chimica Acta. 85(10). 3197-3218 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Tanaka: "An Extended Planar C_5 Conformation and a 3_<10>-Helical Structure of Peptide-Foldamer Constituted of Diverse α-Ethylated α,α-Disubstituted α-Amino Acids"Chemistry, A European Journal. (In press). (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Y.Demizu: "Synthesis of Chiral Cyclic α,α-Disubstituted α-Amino Acid and Its Peptides"Peptide Science 2002. 321-322 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Kurihara: "Prediction of Helical Screw Sense of Oligopeptides Containing Chiral α,α-Disubstituted Amino Acids"Peptide Science 2002. 323-324 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Tanaka: "Conformational Study of Heteropeptide Prepared from Chiral α-Ethylated, α,α-Disubstituted α-Amino Acids"Peptides 2002. 902-903 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Oba: "Conformational Study of Peptides Containing (S)-Ethylleucine as a Chiral α,α-Disubstituted Amino Acid"Peptides 2002. 242-243 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Kurihara: "Computational study on conformation of oligopeptides containing chiral α,α-disubstituted amino acids"Peptides 2002. 786-787 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M. Tanaka, M. Oba, K. Tamai, and H. Suemune,: "Asymmetric Synthesis of α,α-Disubstituted α-Amino Acids Using (S, S)-Cyclohexane-1, 2-diol as a Chiral Auxiliary,"J. Org. Chem.. 66(8). 2667-2673 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M. Tanaka, T. Ichiki, M. Oba, and H. Suemune,: "Solid-State Conformation of a Hybrid Tripeptide Between β-Amino Acid; 8-Aminocyclooct-4-enecarboxylic Acid and 2-Aminoisobutyric Acid"Chem. Pharm. Bull.. 49(9). 1178-1181 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M. Tanaka,: "Design and Conformation of Peptides Containing α,α-Disubstitued α-Amino Acids"J. Synth. Org. Chem. Jpn.. 60. 125-136 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M. Tanaka, M. Oba, M. Kurihara, Y. Demizu, S. Nishimura, K. Hayashida and H. Suemune,: "Asymmetric Synthesis and Conformational Analysis of α,α-Disubstituted α-Amino Acids and Their Peptides"Peptide Science. 2001. 263-266 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M. Kurihara, M. Tanaka, M. Oba, H. Suemune, N. Miyata,: "Conformation of Oligopeptides Containing Chiral α,α-Disubstituted Amino Acide: Computational Study"Peptide Science. 2001. 287-288 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M. Oba, M. Tanaka, M. Kurihara, and H. Suemune,: "Conformation of Peptides Containing a Chiral α-Ethylated α,α-Disubstituted α-Amino Acid: (S)-αEthylleucine (=(2S)-2-Amino-2-ethyl-4-methylpentanoic Acid) within Sequences of Dimethylglycine and Diethylglycine Residues"Helvetica Chimica Acta. 85(10). 3197-3218 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Y. Demizu, M. Tanaka, M. Kurihara, and H. Suemune,: "Synthesis of Chiral Cyclic α,α-Disubstituted α-Amino Acid and Its Peptides"Peptide Science. 2002. 321-322 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M. Kurihara, Y. Sato, A. Matsuzaki, M. Tanaka, M. Oba, Y. Demizu, H. Suemune, and H. Okuda,: "Prediction of Helical Screw Sense of Oligopeptides Containing Chiral α,α-Disubstituted Amino Acids"Peptide Science. 2002. 323-324 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M. Oba, M. Tanaka, M. Kurihara, H. Suemune,: "Conformational study of peptides containing (S)-ethylleucine as a chiral α,α-disubstituted amino acid"Peptides. 2002. 242-243 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M. Kurihara, M. Tanaka, M. Oba, H. Suemune,: "Computational study on conformation of oligopeptides containing chiral α,α-disubstituted amino acids"Peptides. 2002. 786-787 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M. Tanaka, S. Nishimura, M. Oba, Y. Demizu, M. Kurihara, and H. Suemune,: "Conformational study of heteropeptide prepared from chiral α-ethylated α,α-disubstituted α-amino acids"peptides. 2002. 902-903 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M. Tanaka, S. Nishimura, M. Oba, Y. Demizu, M. Kurihara, and H. Suemune,: "An Extended Planar C_5 Conformation and a 3_<10>-Helical Structure of Peptide-Foldamer Constituted of Diverse α-Ethylated α,α-Disubstituted α-Amino Acids, Chemistry"A European Journal. in press. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Oba: "Conformation of Peptides Containing a Chiral α-Ethylated α,α-Disubstituted α-Amino Acid: (S)-αEthylleucine (= (2S)-2-Amino-2-ethyl-4-methylpentanoic Acid) within Sequences of Dimethylglycine and Diethylglycine Residues"Helvetica Chimica Acta. 85(10). 3197-3218 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Tanaka: "An Extended Planar C_5 Conformation and a 3_<10>-Helical Structure of Peptide-Foldamer Constituted of Diverse α-Ethylated α,α-Disubstituted α-Amino Acids"Chemisrty, A European Journal. (In press). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Y.Demizu: "Synthesis of Chiral Cyclic α,α-Disubstituted α-Amino Acid and Its Peptides"Peptide Science 2002. 321-322 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Kurihara: "Prediction of Helical Screw Sense of Oligopeptides Containing Chiral α,α-Disubstituted Amino Acids"Peptide Science 2002. 323-324 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Tanaka: "Conformational Study of Heteropeptide Prepared from Chiral α-Ethylated α,α-Disubstituted α-Amino Acids"Peptides 2002. (In press). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Oba: "Conformational Study of Peptides Containing (S)-Ethylleucine as a Chiral α,α-Disubstituted Amino Acid"Peptides 2002. (In press). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Tanaka: "Asymmetric Synthesis of a, a-Disubstituted a-Amino Acids Using (S, S)-Cyclohexane-1, 2-diol as a Chiral Auxiliary"J. Org. Chem.. 66(8). 2667-2673 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] M.Tanaka: "Solid-State Conformation of a Hybrid Tripeptide Between b-Amino Acid ; 8-Aminocyclooct-4-enecarboxylic Acid and 2-Aminoisobutyric Acid"Chem. Pharm. Bull.. 49(9). 1178-1181 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] 田中正一: "α,α-ジ置換アミノ酸よりなるペプチドのコンフォメーションと分子設計"有機合成化学協会誌. 60. 125-136 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] M.Tanaka: "Asymmetric Synthesis and Conformational Analysis of a, a-Disubstituted a-Amino Acids and Their Peptides"Peptide Science 2001. 263-266 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] M.Kurihara: "Conformation of Oligopeptides Containing Chiral a, a-Disubstituted Amino Acids : Computational Study"Peptide Science 2001. 287-288 (2002)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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