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.
Brard
Mickaëlle
M
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.
Richter
Walter
W
Benvegnu
Thierry
T
Plusquellec
Daniel
D
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