School of Material Science and Chemical Engineering, Harbin Engineering University, Harbin, China.
J Chromatogr A. 2010 Feb 12;1217(7):1041-7. doi: 10.1016/j.chroma.2009.07.027. Epub 2009 Jul 19.
A new class of regioselectively substituted amylose derivatives bearing three different substituents at 2-, 3- and 6-positions, and two different substituents at 2-position and 3-, 6-positions were synthesized by a sequential process based on the esterification of 2-position of a glucose unit. Their chiral recognition abilities were evaluated as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC). Each derivative had its own characteristic recognition ability depending on the arrangement of side chains at the three positions. Among the derivatives, amylose 2-(4-t-butylbenzoate) and amylose 2-(4-chlorobenzoate) series exhibited high chiral recognition. Some racemates can be efficiently separated on these derivatives as well as on the amylose tris-3,5-dimethylphenylcarbamate, which is commercially available as Chiralpak AD and one of the most powerful CSPs. The structures of the amylose derivatives were also investigated by circular dichroism spectroscopy.
一类新型的、在 2-、3-和 6-位具有三个不同取代基，在 2-位和 3-、6-位具有两个不同取代基的、区域选择性取代的直链淀粉衍生物，通过基于葡萄糖单元 2-位酯化的顺序过程合成。它们的手性识别能力作为高效液相色谱（HPLC）的手性固定相（CSP）进行了评估。每个衍生物都具有根据三个位置上侧链的排列而产生的独特的识别能力。在这些衍生物中，直链淀粉 2-（4-叔丁基苯甲酸酯）和直链淀粉 2-（4-氯苯甲酸酯）系列表现出高的手性识别能力。一些外消旋体可以在这些衍生物以及商业上可作为 Chiralpak AD 的、最强大的 CSP 之一的直链淀粉三-3,5-二甲基苯基氨基甲酸酯上有效地分离。直链淀粉衍生物的结构也通过圆二色性光谱进行了研究。
