Cyclohexane Rings Reduce Membrane Permeability to Small Ions in Archaea‐Inspired Tetraether Lipids |
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| Authors: | Takaoki Koyanagi Dr Geoffray Leriche David Onofrei Prof Gregory P Holland Prof Michael Mayer Prof Jerry Yang |
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| Institution: | 1. Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA, USA;2. Department of Chemistry and Biochemistry, San Diego State University, San Diego, CA, USA;3. Department of Biomedical Engineering, University of Michigan, Ann Arbor, MI, USA |
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| Abstract: | Extremophile archaeal organisms overcome problems of membrane permeability by producing lipids with structural elements that putatively improve membrane integrity compared to lipids from other life forms. Herein, we describe a series of lipids that mimic some key structural features of archaeal lipids, such as: 1) single tethering of lipid tails to create fully transmembrane tetraether lipids and 2) the incorporation of small rings into these tethered segments. We found that membranes formed from pure tetraether lipids leaked small ions at a rate that was about two orders of magnitude slower than common bilayer‐forming lipids. Incorporation of cyclopentane rings into the tetraether lipids did not affect membrane leakage, whereas a cyclohexane ring reduced leakage by an additional 40 %. These results show that mimicking certain structural features of natural archaeal lipids results in improved membrane integrity, which may help overcome limitations of many current lipid‐based technologies. |
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| Keywords: | Archaea biomembranes liposomes permeability self-assembly |
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