Abstract
Considerable resistance of archaea to harsh environments is derived from unique cyclic lipids observed in their biomembranes. We have synthesized artificial cyclic lipids that mimic the natural lipids for the purpose of constructing mechanically and thermally stable membranes. The structural features of these lipids include (i) a cyclic framework, (ii) two diacetylene units, (iii) ether (amide) bonds and (iv) two hydrophilic groups. These are the minimum structural elements that would be necessary in order to create functional equivalents of the archaeal lipids. In this paper, we report (i) molecular design, (ii) stereoselective syntheses, and (iii) self-assemblies of the artificial cyclic lipids into various nanostructures including tubules, fibers, and ribbons.
