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Conformational Analysis of Three NK1 Tripeptide Antagonists: A Proton Nuclear Magnetic Resonance Study

Caliendo, G. et al.

Journal of medicinal chemistry. VOL 40; NUMBER 4, ; 1997, 594-601 -- ACS AMERICAN CHEMICAL SOCIETY Part: Part 4; (pages 594-601) -- 1997

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  • Title:
    Conformational Analysis of Three NK1 Tripeptide Antagonists: A Proton Nuclear Magnetic Resonance Study
  • Author: Caliendo, G.;
    Grieco, P.;
    Perissutti, E.;
    Santagada, V.;
    Saviano, G.;
    Tancredi, T.;
    Temussi, P. A.
  • Found In: Journal of medicinal chemistry. VOL 40; NUMBER 4, ; 1997, 594-601
  • Journal Title: Journal of medicinal chemistry.
  • Subjects: Medicine; Biotechnology; Pharmaceutical Chemistry; LCC: RS402; Dewey: 615
  • Publication Details: ACS AMERICAN CHEMICAL SOCIETY
  • Language: English
  • Abstract: Two new peptides, tailored after Ac-Thr-D-Trp(CHO)-Phe-NMeBzl (TRI), namely, Ac-Thr-D-Trp(CHO)-Phe-NMeàMeBzl (TRA) and Ac-Thr-D-Trp(CHO)-Oic-NMeBzl (TOI), in which Phe is replaced by (3aS,7aS)-octahydroindole-2-carboxylic acid, proved more potent and selective NK1 antagonists. The conformational properties of all three compounds were investigated in solution by NMR spectroscopy and those of TRI analyzed in greater detail by means of systematic computer-assisted modeling. All conformers whose energy differs by less than 9 kcal/mol from the absolute minimum are different from the conformer proposed in a previous molecular modeling study by the discoverers of TRI. Parallel calculations for TRA and TOI yield low-energy conformers similar to those of TRI but in a slightly different order. Comparison of the shapes of low-energy conformers of all three peptides with those of four typical rigid NK1 antagonists shows that putative bioactive conformations are indeed present in solution.
  • Identifier: Journal ISSN: 0022-2623
  • Publication Date: 1997
  • Physical Description: Physical
  • Shelfmark(s): 5017.200000
  • UIN: ETOCRN021716558

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