How the Stereochemistry of a Central Cyclopentyl Ring Influences the Self-Assembling Properties of Archaeal Lipid Analogues: Synthesis and CryoTEM Observations
作者:Alicia Jacquemet、Loı̈c Lemiègre、Olivier Lambert、Thierry Benvegnu
DOI:10.1021/jo201827h
日期:2011.12.2
cyclopentane unit placed in the middle of tetraether archaeal bipolar lipid analogues was found to have a dramatic influence on their supramolecular self-assembling properties. The synthesis of two diastereomers varying only by the stereochemistry of the cyclopentyl unit was achieved following a multistep diastereoselective route. The corresponding lipid films were hydrated and were observed by cryoTEM
发现位于四醚古细菌双极性脂质类似物中间的1,3-二取代的环戊烷单元的相对立体化学(顺式或反式)对其超分子自组装性能具有显着影响。遵循多步非对映选择性路线,实现了仅通过环戊基单元的立体化学变化的两种非对映异构体的合成。相应的脂质膜被水合并通过cryoTEM观察。显微照片显示了几种类型的单层纳米物体,例如顺式异构体的薄片或不规则囊泡,而反式异构体则仅显示规则球形的多层囊泡。即使环戊基环是长烷基链(32个碳原子)的一部分,