Advertisement

Two-Dimensional 1H-NMR and CD Structural Analysis in a Micellar Medium of a Bovine αs1-Casein Fragment having Benzodiazepine-Like Properties

Authors

  • Marc Lecouvey,

    1. Laboratoire de Chimie Physique Macromoléculaire, CNRS-URA 494, ENSIC-INPL. Nancy, France
    Search for more papers by this author
  • Céline Frochot,

    1. Laboratoire de Chimie Physique Macromoléculaire, CNRS-URA 494, ENSIC-INPL. Nancy, France
    Search for more papers by this author
  • Laurent Miclo,

    1. Laboratoire des Biosciences de l'Aliment, Unité associée à l'INRA, Université Henri Poincaré-Nancy I, Vandæuvre lès Nancy, France
    Search for more papers by this author
  • Piotr Orlewski,

    1. Laboratoire de Chimie Physique Macromoléculaire, CNRS-URA 494, ENSIC-INPL. Nancy, France
    Search for more papers by this author
  • Alain Driou,

    1. Laboratoire des Biosciences de l'Aliment, Unité associée à l'INRA, Université Henri Poincaré-Nancy I, Vandæuvre lès Nancy, France
    Search for more papers by this author
  • Guy Linden,

    1. Laboratoire des Biosciences de l'Aliment, Unité associée à l'INRA, Université Henri Poincaré-Nancy I, Vandæuvre lès Nancy, France
    Search for more papers by this author
  • Jean-Luc Gaillard,

    1. Laboratoire des Biosciences de l'Aliment, Unité associée à l'INRA, Université Henri Poincaré-Nancy I, Vandæuvre lès Nancy, France
    Search for more papers by this author
  • Michel Marraud,

    1. Laboratoire de Chimie Physique Macromoléculaire, CNRS-URA 494, ENSIC-INPL. Nancy, France
    Search for more papers by this author
  • Manh Thong Cung,

    1. Laboratoire de Chimie Physique Macromoléculaire, CNRS-URA 494, ENSIC-INPL. Nancy, France
    Search for more papers by this author
  • Régis Vanderesse

    Corresponding author
    1. Laboratoire de Chimie Physique Macromoléculaire, CNRS-URA 494, ENSIC-INPL. Nancy, France
      R. Vanderesse, Laboratoire de Chimie Physique Macromoléculaire, CNRS-URA 494, ENSIC-INPL, BP 451, 1 rue Grandville, F-54001 Nancy Cedex, France
      Fax:+33 3 83 37 99 77.
      E-mail:r.vaiideresse@lcpm.ensic.u-na17cy.fr
      URL:http:www.ensic.u-nancy.fr/ENSIC/LCPM/LCPM.html
    Search for more papers by this author

  • Note added in proof. The bioactive peptides from milk have been reviewed recently [Teschemacher, H., Koch, G. & Brantl, v. (1997) Milk protein-derived opioid receptor ligands, Biopolym. Pept. Sci. 43, 99–117; Meisel, H. (1997) Biochemical properties of regulatory peptides derived from milk proteins, Biopolym. Pept. Sci. 43, 119–128]. The bifurcated hydrogen bonds in two intermediate 310/α helices have been described recently [Datta, S., Shamala, N., Banerjee, A. & Balaram, P. (1997) Hydrogen bonds in peptide helices. Analysis of two independent helices in the crystal stnictures of a peptide Boc-Val-Ala-Leu-Aib-Val-Ala-Phe-OMe, J. Pept. Res 49, 604–611].

R. Vanderesse, Laboratoire de Chimie Physique Macromoléculaire, CNRS-URA 494, ENSIC-INPL, BP 451, 1 rue Grandville, F-54001 Nancy Cedex, France
Fax:+33 3 83 37 99 77.
E-mail:r.vaiideresse@lcpm.ensic.u-na17cy.fr
URL:http:www.ensic.u-nancy.fr/ENSIC/LCPM/LCPM.html

Abstract

The conformation of the benzodiazepine-like decapeptide, YLGYLEQLLR, corresponding to residues 91–100 of bovine αs1-casein, has been examined in SDS micelles using CD, two-dimensional 1H-NMR and restrained molecular-dynamics simulation. Evidence is presented that the decapeptide adopts a rigid structure in water/SDS micellar medium, but not in water or dimethylsulfoxide. The three-dimensional structure, consistent with the proton-proton distances obtained from the quantitative analysis of the two-dimensional NOES, was generated by restrained energy minimization and molecular-dynamics simulation. In water/SDS micellar medium, YLCYLEQLLR adopts an amphipathic helicoid structure with distinct hydrophobic and hydrophilic faces. The relative disposition of the tyrosine aromatic rings was compared with that of the aromatic rings in the benzodiazepines.

Ancillary