%0 Journal Article
%T C 9/12 Ribbon-Like Structures in Hybrid Peptides Alternating α- and Thiazole-Based γ-Amino Acids
%+ Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM)
%+ Laboratoire Charles Coulomb (L2C)
%+ Chungbuk National University
%+ Cristallographie, Résonance Magnétique et Modélisations (CRM2)
%+ Centre de Biochimie Structurale [Montpellier] (CBS)
%A Bonnel, Clément
%A Legrand, Baptiste
%A Simon, Matthieu
%A Martinez, Jean
%A Bantignies, Jean-Louis
%A Kang, Young Kee
%A Wenger, Emmanuel
%A Hoh, Francois
%A Masurier, Nicolas
%A Maillard, Ludovic
%< avec comité de lecture
%Z L2C:17-360
%@ 0947-6539
%J Chemistry - A European Journal
%I Wiley-VCH Verlag
%V 23
%N 69
%P 17584-17591
%8 2017-12-11
%D 2017
%R 10.1002/chem.201704001
%K peptides
%K amino acids
%K ribbon structures
%K structure elucidation
%K torsion angles
%Z Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biochemistry [q-bio.BM]
%Z Life Sciences [q-bio]/Biochemistry, Molecular Biology/Structural Biology [q-bio.BM]Journal articles
%X According to their restricted conformational freedom, heterocyclic -amino acids are usually considered to be related to Z-vinylogous -amino acids. In this context, oligomers alternating -amino acids and thiazole-based -amino acids (ATCs) were expected to fold into a canonical 12-helical shape as described for /-hybrid peptides composed of cis-/-unsaturated -amino acids. However, through a combination of X-ray crystallography, NMR spectroscopy, FTIR experiments, and DFT calculations, it was determined that the folding behavior of ATC-containing hybrid peptides is much more complex. The homochiral /(S)-ATC sequences were unable to adopt a stable conformation, whereas the heterochiral /(R)-ATC peptides displayed novel ribbon structures stabilized by unusual C-9/12-bifurcated hydrogen bonds. These ribbon structures could be considered as a succession of pre-organized / dipeptides and may provide the basis for designing original -helix mimics.
%G English
%L hal-02359324
%U https://hal.science/hal-02359324
%~ CNRS
%~ ENSC-MONTPELLIER
%~ IBMM
%~ CBS
%~ L2C
%~ UNIV-LORRAINE
%~ INC-CNRS
%~ CRM2-UL
%~ MIPS
%~ BS
%~ CHIMIE
%~ UNIV-MONTPELLIER
%~ TEST-HALCNRS
%~ UM-2015-2021
%~ BIOLOGIE_ET_AMELIORATION_DES_PLANTES