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Fluorine bonding enhances the energetics of protein-lipid binding in the gas phase Open Access

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Author or creator
Liu, Lan
Jalili, Nobar
Baergen, Alyson
Ng, Simon
Bailey, Justin
Derda, Ratmir
Klassen, John S.
Additional contributors
Subject/Keyword
Protein-ligand complexes
Energetics
Fluorine bonding
Molecular recognition
Hydrophobic interactions
Type of item
Journal Article (Published)
Language
English
Place
Time
Description
This paper reports on the first experimental study of the energies of noncovalent fluorine bonding in a protein-ligand complex in the absence of solvent. Arrhenius parameters were measured for the dissociation of gaseous deprotonated ions of complexes of bovine β-lactoglobulin (Lg), a model lipid-binding protein, and four fluorinated analogs of stearic acid (SA), which contained (X =) 13, 15, 17, or 21 fluorine atoms. In all cases, the activation energies (Ea) measured for the loss of neutral XF-SA from the (Lg + XF-SA)7– ions are larger than for SA. From the kinetic data, the average contribution of each > CF2 group to Ea was found to be ~1.1 kcal mol–1, which is larger than the ~0.8 kcal mol–1 value reported for > CH2 groups. Based on these results, it is proposed that fluorocarbon–protein interactions are inherently stronger (enthalpically) than the corresponding hydrocarbon interactions.
Date created
2014
DOI
doi:10.7939/R3XS5JW0B
License information
© 2014 Liu, L., Jalili, N., Baergen, A., Ng, S., Bailey, J., Derda, R., & Klassen, J. S. This version of this article is open access and can be downloaded and shared. The original author(s) and source must be cited.
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Citation for previous publication
Liu, L., Jalili, N., Baergen, A., Ng, S., Bailey, J., Derda, R., & Klassen, J. S. (2014). Fluorine bonding enhances the energetics of protein-lipid binding in the gas phase. Journal of the American Society for Mass Spectrometry, 25(5), 751-757.  http://doi.org/10.1007/s13361-014-0837-8

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