Synthesis and supramolecular assemblies of bipolar archaeal glycolipid analogues containing a cis-1,3-disubstituted cyclopentane ring.
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.
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.
Mickaëlle
M
Brard
Walter
W
Richter
Thierry
T
Benvegnu
Daniel
D
Plusquellec
D001105:Archaea / Q000737:chemistry*; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry*; D005995:Glyceryl Ethers / Q000138:chemical synthesis / Q000737:chemistry; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry; D008854:Microscopy, Electron
D003517:Cyclopentanes; D005995:Glyceryl Ethers; D006017:Glycolipids; D006027:Glycosides