Amphiphilic cyclodextrins have been synthesized with self-acylating reaction using vinyl esters in dimethylformamide. In the present study no base, catalyst, or enzyme was used, and the structural analyses using thin layer chromatography, nuclear magnetic resonance spectroscopy and mass spectrometry show that the cyclodextrin is substituted preferentially by one acyl moiety at the C2 position of the glucose unit, suggesting that cyclodextrin functions as a regioselective catalytic carbohydrate in organic solvent. In the self-acylation, the most acidic OH group at the 2-position and the inclusion complexing ability of cyclodextrin were considered to be significant. The substrate preference was also observed in favor of the long-chain acyl group, which could be attributed to the inclusion ability of cyclodextrin cavity. Furthermore, using the model amphiphilic building block, 2-O-mono-lauryl β-cyclodextrin, the self-organized supramolecular architecture with nano-vesicular morphology in water was investigated by fluorescence spectroscopy, dynamic light scattering and transmission electron microscopy. The cavity-type nano-assembled vesicle and the novel synthetic methods for the preparation of mono-acylated cyclodextrin should be of great interest with regard to drug/gene delivery systems, functional surfactants, and carbohydrate derivatization methods.

中文翻译：

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在有机溶剂中的区域选择性自酰化环糊精。

使用乙烯基酯在二甲基甲酰胺中的自酰化反应已经合成了两亲环糊精。在本研究中，未使用任何碱，催化剂或酶，并且使用薄层色谱，核磁共振波谱和质谱的结构分析表明，环糊精优先被葡萄糖单元C2位置的一个酰基部分取代，这表明环糊精在有机溶剂中起区域选择性催化碳水化合物的作用。在自酰化中，认为2-位的最酸性OH基和环糊精的包合络合能力很重要。还观察到底物偏爱长链酰基，这可归因于环糊精腔的包容能力。此外，使用模型两亲性结构单元2-O-单月桂基β-环糊精，通过荧光光谱，动态光散射和透射电子显微镜研究了具有纳米水泡形态的自组织超分子结构。关于药物/基因递送系统，功能性表面活性剂和碳水化合物衍生化方法，腔型纳米组装囊泡和制备单酰化环糊精的新颖合成方法应引起人们的极大兴趣。