Stereochemical study on planar-chiral cyclic molecules using polysaccharide-based column chromatography,Chirality

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Stereochemical study on planar-chiral cyclic molecules using polysaccharide-based column chromatography
Chirality ( IF 2.8 ) Pub Date : 2022-04-11 , DOI: 10.1002/chir.23429
Kazunobu Igawa ₁ , Kazuhiro Uehara ₁ , Yuuya Kawasaki ₁ , Katsuhiko Tomooka ₁

Affiliation

The presence of planar chirality of a variety of medium-sized heterocycles, along with nine-membered cyclic ketone and its enol ester, was revealed by observation of isolable enantiomers by analytical high-performance liquid chromatography (HPLC) using a chiral stationary phase with a polysaccharide-based chiral selector. Several tens of milligrams of enantiomers of the planar-chiral molecules were successfully separated by preparative-scale HPLC, leading to the preparation of an enantioenriched sample. This in turn enabled detailed stereochemical studies, including measurement of half-lives of the optical activity and X-ray crystallography for elucidation of stereochemistry.

中文翻译：

基于多糖的柱色谱对平面手性环状分子的立体化学研究

通过使用手性固定相的手性固定相通过分析型高效液相色谱 (HPLC) 观察可分离的对映异构体，揭示了各种中等大小的杂环以及九元环酮及其烯醇酯的平面手性的存在。基于多糖的手性选择器。数十毫克的平面手性分子的对映异构体通过制备级 HPLC 成功分离，从而制备出对映体富集的样品。这反过来又使详细的立体化学研究成为可能，包括测量光学活性的半衰期和用于阐明立体化学的 X 射线晶体学。

更新日期：2022-04-11

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