Modification of bipolar lipid conformation at the air/water interface by a single stereochemical variation

•We studied the behaviours of two bipolar lipids at the air/water interface.•Comparative studies of lipids were done using tensiometry, ellipsometry and AFM.•The stereochemistry of glyceryl moieties was responsible for different behaviours.•Two diastereoisomers have different preferences for bent or stretched conformations.

This article describes the design and the synthesis of two analogues of archaeal bipolar lipids that differ only by the configuration of a single stereogenic centre on a glyceryl moiety. The corresponding comparative physicochemical study by tensiometry/ellipsometry and atomic force microscopy provided a set of data that points out the effect of this single stereochemical variation. The two epimers revealed different conformations at the air/water interface resulting in a more or less tendency for a bent or a stretched conformation. It strengthens the importance of the stereochemistry in such bipolar lipid packing.

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