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Synthesis and Supramolecular Assemblies of Bipolar Archaeal Glycolipid Analogues Containing a cis-1,3-Disubstituted Cyclopentane Ring

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journal contribution
posted on 18.08.2004, 00:00 authored by Mickaëlle Brard, Walter Richter, Thierry Benvegnu, Daniel Plusquellec
Unsymmetrical archaeal tetraether glycolipid analogues 12 incorporating a 1,3-disubstituted cyclopentane ring into the bridging chain have been synthesized. The cyclopentane has been introduced with a totally controlled cis configuration, either into the middle of the aliphatic chain or at three methylene groups from the glycerol unit linked to the bulkier disaccharide residue. Freeze-fracture and cryotransmission electron microscopy experiments clearly demonstrated unprecedented glycolipid supramolecular organizations involving two-by-two monolayer associations coupled with interconnection and fusion phenomena. Furthermore, a significant difference in the hydration properties and in the lyotropic liquid crystalline behavior of bipolar lipids 12 was found depending on the position of the cyclopentane residue.