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Self-Association and Membrane-Binding Behavior of Melittins Containing Trifluoroleucine

Niemz, Angelika and Tirrell, David A. (2001) Self-Association and Membrane-Binding Behavior of Melittins Containing Trifluoroleucine. Journal of the American Chemical Society, 123 (30). pp. 7407-7413. ISSN 0002-7863. doi:10.1021/ja004351p.

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We have investigated the effect of trifluoroleucine substitution on the membrane-binding and tetramerization behavior of melittin. Analogues were synthesized in which Leu 9, Leu 13, and all four intrinsic leucine residues of melittin were replaced by 5,5,5-trifluoroleucine. Both the mono- and tetra-substituted melittins were found to exhibit stronger self-association and enhanced affinity for lipid bilayer membranes, compared to the wild-type peptide. The extent of the observed effects depends on the site of introduction of trifluoroleucine and, in the case of substitution at position 13, on the stereochemistry of the trifluoroleucine side chain. Analysis of the membrane association isotherms is consistent with aggregation of fluorinated melittins within the lipid bilayer. These results suggest that fluorocarbon−hydrocarbon separation, in addition to an increase in hydrophobic character, contributes to enhanced membrane binding.

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Tirrell, David A.0000-0003-3175-4596
Additional Information:Copyright © 2001 American Chemical Society. Received December 27, 2000. Publication Date (Web): July 10, 2001. We would like to acknowledge Dr. Suzanna Horvath, Director of the Caltech Biopolymer Synthesis Center, and her staff for synthesis of the melittin peptides and for performing analytical HPLC measurements. We thank Catherine Sarisky and Dr. Scott Ross for help with the 2D NMR experiments. We are grateful to Yi Tang and Dr. Ilya Koltover for helpful discussions and for providing 5,5,5-trifluoroleucine and synthetic intermediates used in these studies. This work was supported by the U.S. Army Research Office and by a gift from the Dow Chemical Company. A.N. thanks the National Institutes of Health for a postdoctoral fellowship.
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Army Research Office (ARO)UNSPECIFIED
Dow Chemical CompanyUNSPECIFIED
NIH Postdoctoral FellowshipUNSPECIFIED
Issue or Number:30
Record Number:CaltechAUTHORS:NIEjacs2001
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Official Citation:Self-Association and Membrane-Binding Behavior of Melittins Containing Trifluoroleucine Angelika Niemz and and David A. Tirrell Journal of the American Chemical Society 2001 123 (30), 7407-7413
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:53356
Deposited By: Anne Hormann
Deposited On:07 Feb 2015 01:22
Last Modified:10 Nov 2021 20:00

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