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Lipopeptaibol metabolites of tolypocladium geodes: total synthesis, preferred conformation, and membrane activity.
- Source :
-
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2003 Aug 04; Vol. 9 (15), pp. 3567-76. - Publication Year :
- 2003
-
Abstract
- We have synthesized by solution methods and characterized the lipopeptaibol metabolite LP237-F8 extracted from the fungus Tolypocladium geodes and five selected analogues with the Etn-->Aib or Etn-->Nva replacement at position 8 and/or a triple Gln-->Glu(OMe) replacement at positions 5, 6, and 9 (Etn=Calpha-ethylnorvaline, Aib=alpha-aminoisobutyric acid, Nva=norvaline). Conformation analysis, performed by FT-IR absorption, NMR, and CD techniques, strongly supports the view that the six terminally blocked decapeptides are highly helical in solution. Helix topology and amphiphilic character are responsible for their remarkable membrane activity. At position 8 the combination of high hydrophobicity and Calpha tetrasubstitution, as in the Etn-containing LP237-F8 metabolite, has a positive effect on membrane interaction.
- Subjects :
- Amino Acid Sequence
Anti-Bacterial Agents chemistry
Anti-Bacterial Agents metabolism
Anti-Bacterial Agents pharmacology
Cell Membrane Permeability
Circular Dichroism
Fluorescent Dyes chemistry
Hydrogen Bonding
Membranes, Artificial
Mitosporic Fungi metabolism
Models, Molecular
Nuclear Magnetic Resonance, Biomolecular
Peptaibols
Phosphatidylcholines chemistry
Phosphatidylcholines metabolism
Phospholipids chemistry
Phospholipids metabolism
Protein Conformation
Spectrometry, Fluorescence
Spectroscopy, Fourier Transform Infrared
Anti-Bacterial Agents chemical synthesis
Mitosporic Fungi chemistry
Peptides
Subjects
Details
- Language :
- English
- ISSN :
- 0947-6539
- Volume :
- 9
- Issue :
- 15
- Database :
- MEDLINE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Publication Type :
- Academic Journal
- Accession number :
- 12898683
- Full Text :
- https://doi.org/10.1002/chem.200304756