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通过手性柱HPLC分析炔烃对映体的钴配合物实现炔烃对映体的分离。

Separation of Alkyne Enantiomers by Chiral Column HPLC Analysis of Their Cobalt-Complexes.

作者信息

Liu Qiaoyun, Wang Jing, Li Junfei, Wang Xiaolei, Lu Shichao, Li Xuan, Gong Yaling, Xu Shu

机构信息

School of Chemistry and Material Science, Shanxi Normal University, 1 Gongyuan Street, Linfen, Shanxi 041004, China.

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 2A NanWei Road, Xicheng Distrct, Beijing 100050, China.

出版信息

Molecules. 2017 Mar 20;22(3):466. doi: 10.3390/molecules22030466.

Abstract

Separation of the enantiomers of new chiral alkynes in strategic syntheses and bioorthogonal studies is always problematic. The chiral column high-performance liquid chromatography (HPLC) method in general could not be directly used to resolve such substrates, since the differentiation of the alkyne segment with the other alkane/alkene segment is not significant in the stationary phase, and the alkyne group is not a good UV chromophore. Usually, a pre-column derivatization reaction with a tedious workup procedure is needed. Making use of easily-prepared stable alkyne-cobalt-complexes, we developed a simple and general method by analyzing the in situ generated cobalt-complex of chiral alkynes using chiral column HPLC. This new method is especially suitable for the alkynes without chromophores and other derivable groups.

摘要

在策略性合成和生物正交研究中,分离新型手性炔烃的对映体一直存在问题。一般来说,手性柱高效液相色谱(HPLC)方法不能直接用于拆分此类底物,因为在固定相中炔烃片段与其他烷烃/烯烃片段的差异不显著,并且炔基不是良好的紫外发色团。通常,需要进行繁琐后处理程序的柱前衍生化反应。利用易于制备的稳定炔烃 - 钴配合物,我们开发了一种简单通用的方法,即使用手性柱HPLC分析手性炔烃原位生成的钴配合物。这种新方法特别适用于没有发色团和其他可衍生基团的炔烃。

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