title: A ring to rule them all: the effect of cyclopropane Fatty acids on the fluidity of lipid bilayers.
abstract: Cyclopropane fatty acids are widespread in bacteria. As their concentration increases on exposure to hostile environments, they have been proposed to protect membranes. Here, the effect of cyclopropane and unsaturated fatty acids, both in cis and trans configurations, on the packing, order, and fluidity of lipid bilayers is explored using molecular dynamics simulations. It is shown that cyclopropane fatty acids disrupt lipid packing, favor the occurrence of gauche defects in the chains, and increase the lipid lateral diffusion, suggesting that they enhance fluidity. At the same time, they generally induce a greater degree of order than unsaturated fatty acids of the same configuration and limit the rotation about the bonds surrounding the cyclopropane ring. This indicates that cyclopropane fatty acids may fulfill a dual function: stabilizing membranes against adverse conditions while simultaneously promoting their fluidity. Marked differences in the effect of cis- and trans-monocyclopropanated fatty acids were also observed, suggesting that they may play alternative roles in membranes.
authors: †School of Chemistry and Molecular Biosciences and ‡Institute for Molecular Bioscience, The University of Queensland, Brisbane QLD 4072, Australia.
authors: David
authors: D
authors: Poger
authors: †School of Chemistry and Molecular Biosciences and ‡Institute for Molecular Bioscience, The University of Queensland, Brisbane QLD 4072, Australia.
authors: Alan E
authors: AE
authors: Mark
mesh_terms: D003521:Cyclopropanes / Q000494:pharmacology*; D005227:Fatty Acids / Q000494:pharmacology*; D008051:Lipid Bilayers / Q000737:chemistry*; D008560:Membrane Fluidity / Q000187:drug effects*; D008968:Molecular Conformation; D056004:Molecular Dynamics Simulation; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D005227:Fatty Acids; D008051:Lipid Bilayers; C028775:cyclopropane fatty acids