Bolalipids, or archaeal-type phospholipids, are unique materials which form fluid lamellar-phase membranes with enhanced stability over membranes formed from more conventional monopolar phospholipids. This enhanced stability presumably comes from 1) an ether-linkage between the glycerol backbone and the hydrophobic region of the lipid and 2) the presence of transmembrane spanning alkyl group(s).  Bolalipids have demonstrated potential in applications such as lipid membrane-based biosensors, drug-, gene- and vaccine delivery vehicles, and as molecular fossils.  Despite some recent advances; the structure-function properties of bolalipids are poorly understood.  Two bolalipids, C22BAS and C24BAS, are synthesized to gain a fundamental understanding of the effects of alkyl length on the physical properties of the resulting membranes.  Similar synthetic strategies used to synthesize the previously generated bolalipids, C20BAS and C32BAS, are employed.

Synthesis of archaeal-type phospholipids with varying alkyl chain lengths

241st National Meeting (2011)

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