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接枝于全甲基化β-环糊精衍生物上的(L)-或(D)-缬氨酸叔丁酰胺作为新型混合二元手性选择剂:毛细管气相色谱对映体分离的通用工具

(L)- or (D)-valine tert-butylamide grafted on permethylated beta-cyclodextrin derivatives as new mixed binary chiral selectors: versatile tools for capillary gas chromatographic enantioseparation.

作者信息

Stephany O, Dron F, Tisse S, Martinez A, Nuzillard J-M, Peulon-Agasse V, Cardinaël P, Bouillon J-P

机构信息

UPRES EA 3233, Sciences et Méthodes Séparatives, I.R.C.O.F., Université de Rouen, F-76821 Mont Saint Aignan Cedex, France.

出版信息

J Chromatogr A. 2009 May 1;1216(18):4051-62. doi: 10.1016/j.chroma.2009.02.090. Epub 2009 Mar 5.

Abstract

This work deals with the synthesis of two mixed binary chiral selectors prepared by grafting (L)- or (D)-valine tert-butylamide on permethylated cyclodextrin macrocycle. The enantioselective properties of the new chiral selectors diluted in OV11 polysiloxane (35% phenyl- and 65% methylsiloxane) were investigated by means of injections of 117 racemic mixtures. The mixed chiral selectors with (L)-valine and, to a lesser extent with (D)-valine, were found to have an improved enantioselectivity toward amino acid derivatives by comparison to permethylated cyclodextrin. The enantioseparation capability of these new chiral selectors has proven to be slightly less efficient than Chirasil-L-Val (Alltech) for amino acid derivatives, but it has been extended to include terpenes, lactones, esters, aliphatic compounds and aryl alcohols.

摘要

这项工作涉及两种混合二元手性选择剂的合成,它们是通过将(L)-或(D)-缬氨酸叔丁酰胺接枝到全甲基化环糊精大环上制备而成的。通过注入117种外消旋混合物,研究了稀释在OV11聚硅氧烷(35%苯基和65%甲基硅氧烷)中的新型手性选择剂的对映选择性。与全甲基化环糊精相比,发现含有(L)-缬氨酸的混合手性选择剂,以及在较小程度上含有(D)-缬氨酸的混合手性选择剂,对氨基酸衍生物具有更高的对映选择性。已证明这些新型手性选择剂对氨基酸衍生物的对映体分离能力略低于Chirasil-L-Val(安捷伦科技公司),但已扩展到包括萜类、内酯、酯、脂肪族化合物和芳醇。

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