Preventing leakage of small molecules and ions across membranes is a major challenge in both nature and artificial systems. Archaea organisms have evolved to solve membrane permeability problems by producing unique lipid structures and compositions that collectively lead to improved integrity of their membranes compared to eukaryotic organisms. This work describes the synthesis and evaluation of permeability of a series of lipids that mimic the unique structural features that distinguish Archaea-derived lipids from prokaryotic or eukaryotic lipids. In particular, we will present studies on small ion permeability of liposomes derived from lipids that included small rings incorporated into tetraether lipids. From the study, leakage rates of small ions were obtained from a set of synthetic lipids to probe the effects of ring type (cyclopropane or cyclohexane) and number of rings incorporated into the lipids. The results suggest that incorporation of certain structural elements found in Archaea into lipids can translate into large reductions in membrane permeability, which may help overcome some limitations of many lipid-based technologies and devices.

Cyclohexane rings reduce small ion membrane permeability in archaea-inspired tetraether lipids

251st National Meeting (2016)

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