Impact of a stereocentre inversion in cyclic lipodepsipeptides from the viscosin group: a comparative study of the viscosinamide and pseudodesmin conformation and self-assembly
- Author
- Niels Geudens (UGent) , Matthias De Vleeschouwer (UGent) , Krisztina Fehér (UGent) , Hassan Rokni-Zadeh, Maarten GK Ghequire, Annemieke Madder (UGent) , René De Mot, José Martins (UGent) and Davy Sinnaeve (UGent)
- Organization
- Abstract
- The viscosin group covers a series of cyclic lipodepsipeptides (CLPs) produced by Pseudomonas bacteria, with a range of biological functions and antimicrobial activities. Their oligopeptide moieties are composed of both l- and d-amino acids. Remarkably, the Leu5 amino acid-centrally located in the nonapeptide sequence-is the sole residue found to possess either an l or d configuration, depending on the producing strain. The impact of this D/L switch on the solution conformation was investigated by NMR-restrained molecular modelling of the epimers pseudodesmin A and viscosinamide A. Although the backbone fold remained unaffected, the D/L switch adjusted the segregation between hydrophobic and hydrophilic residues, and thus the amphipathicity. It also influenced the self-assembly capacity in organic solvents. Additionally, several new minor variants of viscosinamide A from Pseudomonas fluorescens DR54 were identified, and an NMR assay is proposed to assess the presence of either an L- or D-Leu5.
- Keywords
- ANTIBACTERIAL AGENTS, BIOLOGICAL-ACTIVITY, LIPOPEPTIDE PRODUCTION, BIOSURFACTANT VISCOSIN, COUPLING-CONSTANTS, SUGAR-BEET RHIZOSPHERE, PSEUDOMONAS-FLUORESCENS DR54, LINE-INDUCING PRINCIPLE, conformation, viscosin group, viscosinamide, pseudodesmin, cyclic lipodepsipeptide, pseudomonas, NMR spectroscopy, NMR-SPECTROSCOPY, PSEUDOPHOMIN-B
Downloads
-
(...).pdf
- full text
- |
- UGent only
- |
- |
- 7.18 MB
Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-5799910
- MLA
- Geudens, Niels, et al. “Impact of a Stereocentre Inversion in Cyclic Lipodepsipeptides from the Viscosin Group: A Comparative Study of the Viscosinamide and Pseudodesmin Conformation and Self-Assembly.” CHEMBIOCHEM, vol. 15, no. 18, 2014, pp. 2736–46, doi:10.1002/cbic.201402389.
- APA
- Geudens, N., De Vleeschouwer, M., Fehér, K., Rokni-Zadeh, H., Ghequire, M. G., Madder, A., … Sinnaeve, D. (2014). Impact of a stereocentre inversion in cyclic lipodepsipeptides from the viscosin group: a comparative study of the viscosinamide and pseudodesmin conformation and self-assembly. CHEMBIOCHEM, 15(18), 2736–2746. https://doi.org/10.1002/cbic.201402389
- Chicago author-date
- Geudens, Niels, Matthias De Vleeschouwer, Krisztina Fehér, Hassan Rokni-Zadeh, Maarten GK Ghequire, Annemieke Madder, René De Mot, José Martins, and Davy Sinnaeve. 2014. “Impact of a Stereocentre Inversion in Cyclic Lipodepsipeptides from the Viscosin Group: A Comparative Study of the Viscosinamide and Pseudodesmin Conformation and Self-Assembly.” CHEMBIOCHEM 15 (18): 2736–46. https://doi.org/10.1002/cbic.201402389.
- Chicago author-date (all authors)
- Geudens, Niels, Matthias De Vleeschouwer, Krisztina Fehér, Hassan Rokni-Zadeh, Maarten GK Ghequire, Annemieke Madder, René De Mot, José Martins, and Davy Sinnaeve. 2014. “Impact of a Stereocentre Inversion in Cyclic Lipodepsipeptides from the Viscosin Group: A Comparative Study of the Viscosinamide and Pseudodesmin Conformation and Self-Assembly.” CHEMBIOCHEM 15 (18): 2736–2746. doi:10.1002/cbic.201402389.
- Vancouver
- 1.Geudens N, De Vleeschouwer M, Fehér K, Rokni-Zadeh H, Ghequire MG, Madder A, et al. Impact of a stereocentre inversion in cyclic lipodepsipeptides from the viscosin group: a comparative study of the viscosinamide and pseudodesmin conformation and self-assembly. CHEMBIOCHEM. 2014;15(18):2736–46.
- IEEE
- [1]N. Geudens et al., “Impact of a stereocentre inversion in cyclic lipodepsipeptides from the viscosin group: a comparative study of the viscosinamide and pseudodesmin conformation and self-assembly,” CHEMBIOCHEM, vol. 15, no. 18, pp. 2736–2746, 2014.
@article{5799910,
abstract = {{The viscosin group covers a series of cyclic lipodepsipeptides (CLPs) produced by Pseudomonas bacteria, with a range of biological functions and antimicrobial activities. Their oligopeptide moieties are composed of both l- and d-amino acids. Remarkably, the Leu5 amino acid-centrally located in the nonapeptide sequence-is the sole residue found to possess either an l or d configuration, depending on the producing strain. The impact of this D/L switch on the solution conformation was investigated by NMR-restrained molecular modelling of the epimers pseudodesmin A and viscosinamide A. Although the backbone fold remained unaffected, the D/L switch adjusted the segregation between hydrophobic and hydrophilic residues, and thus the amphipathicity. It also influenced the self-assembly capacity in organic solvents. Additionally, several new minor variants of viscosinamide A from Pseudomonas fluorescens DR54 were identified, and an NMR assay is proposed to assess the presence of either an L- or D-Leu5.}},
author = {{Geudens, Niels and De Vleeschouwer, Matthias and Fehér, Krisztina and Rokni-Zadeh, Hassan and Ghequire, Maarten GK and Madder, Annemieke and De Mot, René and Martins, José and Sinnaeve, Davy}},
issn = {{1439-4227}},
journal = {{CHEMBIOCHEM}},
keywords = {{ANTIBACTERIAL AGENTS,BIOLOGICAL-ACTIVITY,LIPOPEPTIDE PRODUCTION,BIOSURFACTANT VISCOSIN,COUPLING-CONSTANTS,SUGAR-BEET RHIZOSPHERE,PSEUDOMONAS-FLUORESCENS DR54,LINE-INDUCING PRINCIPLE,conformation,viscosin group,viscosinamide,pseudodesmin,cyclic lipodepsipeptide,pseudomonas,NMR spectroscopy,NMR-SPECTROSCOPY,PSEUDOPHOMIN-B}},
language = {{eng}},
number = {{18}},
pages = {{2736--2746}},
title = {{Impact of a stereocentre inversion in cyclic lipodepsipeptides from the viscosin group: a comparative study of the viscosinamide and pseudodesmin conformation and self-assembly}},
url = {{http://dx.doi.org/10.1002/cbic.201402389}},
volume = {{15}},
year = {{2014}},
}
- Altmetric
- View in Altmetric
- Web of Science
- Times cited: