Reinforcing effect of bi- and tri-cyclopolyprenols on ‘primitive’ membranes made of polyprenyl phosphates

Cholesterol plays the role of membrane reinforcer in eukaryotes, whereas hopanoids play the same role in bacteria. Which components could have reinforced ‘primitive’ membranes? We describe here an efficient biomimetic synthesis of bi- and tri-cyclopolyprenols and demonstrate that these compounds rei...

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Bibliographic Details
Published in:Tetrahedron 2007-04, Vol.63 (16), p.3395-3407
Main Authors: Ribeiro, Nigel, Streiff, Stéphane, Heissler, Denis, Elhabiri, Mourad, Albrecht-Gary, Anne Marie, Atsumi, Michiko, Gotoh, Mari, Désaubry, Laurent, Nakatani, Yoichi, Ourisson, Guy
Format: Article
Language:English
Subjects:
Biomimetic synthesis
Chemical Sciences
Lipids
Membranes
Organic chemistry
Terpenes
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Summary:Cholesterol plays the role of membrane reinforcer in eukaryotes, whereas hopanoids play the same role in bacteria. Which components could have reinforced ‘primitive’ membranes? We describe here an efficient biomimetic synthesis of bi- and tri-cyclopolyprenols and demonstrate that these compounds reinforce the membranes of polyprenyl phosphate, which we speculated as ‘primitive’ membranes. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.01.076