Synthesis and supramolecular assemblies of bipolar archaeal glycolipid analogues containing a cis-1,3-disubstituted cyclopentane ring |
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Authors: | Brard Mickaëlle Richter Walter Benvegnu Thierry Plusquellec Daniel |
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Institution: | Ecole Nationale Supérieure de Chimie de Rennes, Synthèses et Activations de Biomolécules, CNRS UMR 6052, Institut de Chimie de Rennes, Avenue du Général Leclerc, 35700 Rennes, France. |
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Abstract: | Unsymmetrical archaeal tetraether glycolipid analogues 1-2 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 1-2 was found depending on the position of the cyclopentane residue. |
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