Tetraether lipids (bolalipids) are lipids naturally found in Archaea and form significantly more stable membranes than those formed from conventional monopolar phospholipids.  These materials can help address the morphological instability of membrane-based biosensors.  Unfortunately, the structure-function relationships of these materials are poorly understood, particularly with regards to the symmetry, or lack thereof, of the bipolar lipid.  In order to help address this deficiency, we are interested in synthesizing asymmetric bolalipids containing either differing headgroups on each terminus and/or differing alkyl chains on the 2 and 2� positions of opposing glycerol subunits.  We report the progress towards the synthesis of an asymmetric bolalipid with a single 24-carbon transmembrane spanning chain and two different headgroups: a phosphatidylcholine and a phosphatidylethanolamine.  This compound will be analyzed for its membrane biophysical properties.

Synthesis of a tetraether glycerophospholipid with two different headgroups

247th National Meeting (2014)

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