As opposed to natural archaeal tethered lipids, which typically contain two transmembrane tethers to form a C-40 macrocyclic lipid (5), we synthesized and studied bipolar hemi-macrocyclic lipids (5) containing a single transmembrane tether between lipid tails; these are synthetically more accessible on the gram scale than fully macrocyclic archaeal lipids (25). Specifically, we generated three lipids that all contained a phytanyl acyl chain, an ether linkage to a glycerol, and a phosphocholine head group (fig. S1A). We chose phosphocholine as a head group to increase the probability of forming stable liposomes (26). We chose ether linkages to match the ether linkages that are found in archaea, which increase the chemical (i.e., hydrolytic) stability of lipids (6). We incorporated an untethered phytanyl acyl chain (as opposed to a saturated hydrocarbon chain without methyl groups) into all lipids to reduce the probability of a phase transition in the temperature range of interest (6) and to avoid phase transition–induced leakage (2729). This design made it possible to generate lipids T32, T36, and U16 in ~10 synthetic steps, as previously described (10).

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