222984-24-9Relevant academic research and scientific papers
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.
An efficient synthesis of analogues of unsymmetrical archaeal tetraether glycolipids
Lecollinet, Gregory,Auzely-Velty, Rachel,Benvegnu, Thierry,Mackenzie, Grahame,Goodby, John W.,Plusquellec, Daniel
, p. 1571 - 1572 (2007/10/03)
Unsymmetrical tetraether analogues of glycolipids found in archaebacteria, possessing either two different carbohydrate units or a saccharidic moiety and a phosphate group as polar heads and a quasi-macrocyclic lipid core, are efficiently synthesized from
