222984-22-7Relevant academic research and scientific papers
Synthesis and supramolecular assemblies of bipolar archaeal glycolipid analogues containing a cis-1,3-disubstituted cyclopentane ring
Brard, Mickaelle,Richter, Walter,Benvegnu, Thierry,Plusquellec, Daniel
, p. 10003 - 10012 (2007/10/03)
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
Supramolecular self-assembling properties of membrane-spanning archaeal tetraether glycolipid analogues
Lecollinet, Gregory,Gulik, Annette,Mackenzie, Grahame,Goodby, John W.,Benvegnu, Thierry,Plusquellec, Daniel
, p. 585 - 593 (2007/10/03)
The self-assembling properties of a new series of archaeal tetraether glycolipid analogues 1-6 that are characterized by a bipolar architecture with two similar or different glycosidic and/or phosphate polar heads and a lipid core possessing a cyclopentan
Synthetic approaches to novel archaeal tetraether glycolipid analogues
Lecollinet, Gregory,Auzely-Velty, Rachel,Danel, Mathieu,Benvegnu, Thierry,Mackenzie, Grahame,Goodby, John W.,Plusquellec, Daniel
, p. 3139 - 3150 (2007/10/03)
Symmetrical and unsymmetrical archaeal tetraether glycolipid analogues have been prepared. The syntheses are based upon the elaboration of lipid cores from versatile chiral starting materials followed by simultaneous or sequential introduction of polar headgroups. Three pathways (A-C) were elaborated for the synthesis of stereochemically defined lipids 14-16 characterized by a straight bridging spacer and two dihydrocitronellyl chains attached to glycerol units at the sn-3 and sn-2 positions, respectively. Pathway C appeared to be particularly advantageous for the synthesis of tetraether 9, which possesses a cyclopentane unit as found in thermoacidophilic lipids. Diglycosylated lipids 4-6 were produced in 49-53% yields by reaction of diols 14-16 with β-Dgalactofuranosyl donor 31, whereas unsymmetrical lipids possessing either two different carbohydrate units 7 or a saccharidic moiety and a phosphate group 8 were efficiently prepared from monoprotected diol 35. These compounds represent the first examples of tetraether-type analogues containing a phosphate unit and/or glycosyl moieties.
