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首页> 外文期刊>Chirality: The pharmacological, biological, and chemical consequences of molecular asymmetry >Gas-chromatographic approach to probe the absence of molecular inclusion in enantioseparations by carbohydrates. Investigation of linear dextrins ('acyclodextrins') as novel chiral stationary phases
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Gas-chromatographic approach to probe the absence of molecular inclusion in enantioseparations by carbohydrates. Investigation of linear dextrins ('acyclodextrins') as novel chiral stationary phases

机译：气相色谱法检测碳水化合物对映体分离中是否存在分子夹杂。线性糊精（“ acyclodextrins”）作为新型手性固定相的研究

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摘要

Acetylated/silylated maltooligosaccharides with different degrees of oligomerization have been tested as chiral stationary phases for enantioselective gas chromatography. The acyclic dextrin derivatives carrying tert-butyldimethylsilyl groups at the primary hydroxyl sites and acetyl groups at the secondary hydroxyl sites showed an unexpected ability for the enantioseparation of alpha-amino acid derivatives and halogenated compounds, in addition to some underivatized chiral compounds. Some examples of an improved enantioselectivity invoked by the linear CSPs as compared to that of cyclic oligosaccharides are demonstrated in this work. The results highlight the role of the polar external surface of the selector in lieu of the well-established inclusion mechanism of enantiorecognition by cyclic dextrins. Thus, the enantioseparation of chiral compounds on linear dextrin derivatives-devoid of a molecular cavity-sheds a new light on the mechanisms of enantiorecognition by cyclodextrin derivatives. In contrast to cyclodextrins, linear dextrins are readily accessible in both enantiomeric forms.
机译：具有不同低聚度的乙酰化/甲硅烷基低聚麦芽糖已被测试为手性固定相，用于对映选择性气相色谱。除一些未衍生的手性化合物外，在伯羟基位上带有叔丁基二甲基甲硅烷基而在仲羟基位上带有乙酰基的无环糊精衍生物显示出对映体分离α-氨基酸衍生物和卤代化合物的出乎意料的能力。这项工作证明了与环状寡糖相比，线性CSP所提高的对映选择性的一些实例。结果突出了选择器的极性外表面的作用，代替了已建立的环状糊精对映体识别的包涵机制。因此，在线性糊精衍生物上的手性化合物的对映体分离-没有分子腔-揭示了环糊精衍生物对映体识别的机理。与环糊精相反，两种对映体形式的线性糊精都容易获得。

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