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Article

Conformation and Dynamics of the Cyclic Lipopeptide Viscosinamide at the Water-Lipid Interface

1
NMR and Structural Analysis Unit, Department of Organic and Macromolecular Chemistry, Ghent University, Campus Sterre, S4, Krijgslaan 281, B-9000 Gent, Belgium
2
CNRS, UMR 8576 Unité de Glycobiologie Structurale et Fonctionnelle, Université de Lille, 59000 Lille, France
3
Laboratory of Phytopathology, Department of Plants and Crops, Ghent University, Coupure Links 653, B-9000 Gent, Belgium
*
Author to whom correspondence should be addressed.
These authors contributed equally to the work.
Academic Editor: Theodore Tselios
Molecules 2019, 24(12), 2257; https://doi.org/10.3390/molecules24122257
Received: 18 May 2019 / Revised: 11 June 2019 / Accepted: 13 June 2019 / Published: 17 June 2019
(This article belongs to the Special Issue Cyclic Peptide Analogues and Non-peptide Mimetics)
Cyclic lipodepsipeptides or CLiPs from Pseudomonas are secondary metabolites that mediate a wide range of biological functions for their producers, and display antimicrobial and anticancer activities. Direct interaction of CLiPs with the cellular membranes is presumed to be essential in causing these. To understand the processes involved at the molecular level, knowledge of the conformation and dynamics of CLiPs at the water-lipid interface is required to guide the interpretation of biophysical investigations in model membrane systems. We used NMR and molecular dynamics to study the conformation, location and orientation of the Pseudomonas CLiP viscosinamide in a water/dodecylphosphocholine solution. In the process, we demonstrate the strong added value of combining uniform, isotope-enriched viscosinamide and protein NMR methods. In particular, the use of techniques to determine backbone dihedral angles and detect and identify long-lived hydrogen bonds, establishes that the solution conformation previously determined in acetonitrile is maintained in water/dodecylphosphocholine solution. Paramagnetic relaxation enhancements pinpoint viscosinamide near the water-lipid interface, with its orientation dictated by the amphipathic distribution of hydrophobic and hydrophilic residues. Finally, the experimental observations are supported by molecular dynamics simulations. Thus a firm structural basis is now available for interpreting biophysical and bioactivity data relating to this class of compounds. View Full-Text
Keywords: pseudomonas; viscosinamide; conformation; NMR spectroscopy; isotopic labelling pseudomonas; viscosinamide; conformation; NMR spectroscopy; isotopic labelling
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MDPI and ACS Style

Geudens, N.; Kovács, B.; Sinnaeve, D.; Oni, F.E.; Höfte, M.; Martins, J.C. Conformation and Dynamics of the Cyclic Lipopeptide Viscosinamide at the Water-Lipid Interface. Molecules 2019, 24, 2257. https://doi.org/10.3390/molecules24122257

AMA Style

Geudens N, Kovács B, Sinnaeve D, Oni FE, Höfte M, Martins JC. Conformation and Dynamics of the Cyclic Lipopeptide Viscosinamide at the Water-Lipid Interface. Molecules. 2019; 24(12):2257. https://doi.org/10.3390/molecules24122257

Chicago/Turabian Style

Geudens, Niels, Benjámin Kovács, Davy Sinnaeve, Feyisara E. Oni, Monica Höfte, and José C. Martins. 2019. "Conformation and Dynamics of the Cyclic Lipopeptide Viscosinamide at the Water-Lipid Interface" Molecules 24, no. 12: 2257. https://doi.org/10.3390/molecules24122257

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