Tetraether lipids (or bipolar lipids) are a growing set of materials used to enhance the stability of membranes in membrane-based biotechnologies.  Most of these bipolar lipids are symmetric in nature, i.e., the lipids contain identical headgroups and alkyl chains on either side of the lipid.  Due to limited synthetic precedence for the synthesis of asymmetric lipids, little is known about the impact of intrinsic curvature of tetraether lipids on membrane morphology.  We report progress towards the synthesis of asymmetric lipids via two synthetic routes: one which utilizes a cross-metathesis reaction and the other a Wittig reaction as key transformations.  Once generated, the biophysical properties of membranes formed from these asymmetric lipids will be evaluated.

Synthesis of asymmetric tetraether lipids through cross-metathesis and Wittig reactions

245th National Meeting (2013)

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