Stereochemical effect revealed in self-assemblies based on archaeal lipid analogues bearing a central five-membered carbocycle: a SAXS study. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Langmuir Année : 2012

Stereochemical effect revealed in self-assemblies based on archaeal lipid analogues bearing a central five-membered carbocycle: a SAXS study.

Résumé

The relative stereochemistry (cis or trans) of a 1,3-disubstituted cyclopentane unit in the middle of tetraether archaeal bipolar lipid analogues was found to have a dramatic influence on their supramolecular self-assembly properties. SAXS studies of two synthetic diastereomeric archaeal lipids bearing two lactosyl polar head groups at opposite ends revealed different lyotropic behaviors. The cis isomer led to L(c)-L(α)-Q(II) transitions whereas the trans isomer retained an L(α) phase from 20 to 100 °C. These main differences originate from the conformational equilibrium (pseudorotation) of 1,3-disubstituted cyclopentanes. Indeed, this pseudorotation exhibits quite similar orientations of the two substituents in a trans isomer whereas several orientations of the two alkyl chains are expected in a cis-1,3-dialkyl cyclopentane, thus authorizing more conformational flexibility in the lipid packing.

Domaines

Chimie organique
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Dates et versions

hal-00904782 , version 1 (15-11-2013)

Identifiants

Citer

Alicia Jacquemet, Cristelle Meriadec, Loïc Lemiègre, Franck Artzner, Thierry Benvegnu. Stereochemical effect revealed in self-assemblies based on archaeal lipid analogues bearing a central five-membered carbocycle: a SAXS study.. Langmuir, 2012, 28 (20), pp.7591-7597. ⟨10.1021/la2045948⟩. ⟨hal-00904782⟩
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