Tetraether lipids, or bolalipids, occur naturally in archaeal-membranes and have significant potential in membrane-based biotechnology, such as biosensors and drug delivery vehicles.  The enhanced stability of these lipids can be attributed to ether linkages between the glycerol backbone and lipid chain and the presence of transmenbrane alkyl chain(s).  In attempts to generate a more complete understanding of the structure/function relationships between bolalipids and their resulting membranes, bolalipids of varying alkyl chain lengths are synthesized.  We report progress on the synthesis of three lipids, C16BAS, C24BAS, and C28BAS.  Further, we describe the synthesis of bisfunctionalized C12 and C14 alkanes, necessary precursors for the synthesis of these tetraether lipids.  With the help of the previously synthesized bolalipids, C20BAS and C32BAS, we will use these bolalipids to probe the effects of chain length on the biophysical properties of their membranes.

Synthesis of straight-chain bolalipids with varying alkyl chain length

243rd National Meeting (2012)

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