Preparation method of chiral ligand exchange chromatographic stationary phase

Abstract

A process for using L-isoleucine as the chiral selective agent to prepare the stationary phase for chiral ligand displacement chromatography is disclosed. Its advantages are simple operation (directly splitting the chiral substance in simple experimental condition), high analysis speed, and wide application range.

Description

technical field [0001] The invention relates to the separation of amino acid enantiomers, in particular to a preparation method of a chiral ligand exchange chromatographic stationary phase. Background technique [0002] The separation of amino acid enantiomers can be done by gas chromatography and liquid chromatography, but usually requires pre-column sample derivatization. The derivatization process is not only time-consuming and troublesome, but also may cause racemization of the analyte, thereby affecting the analysis effect . Chiral Ligand Exchange Chromatography (CLEC), developed by Davankov et al. in the early 1970s, is an effective method for separating chiral compounds, especially amino acids and hydroxyacid enantiomers, with high selectivity, No pre-column derivatization is required. [0003] The coating and preparation of bonded phases using photoactive amino acids or pipecolic acid as chiral selectors are the mainstream in the development of chiral ligand exchan...

AI Technical Summary

Problems solved by technology

Chinese patent application (application number 99117305.8) discloses a chiral ligand exchange chromatography stationary phase and a preparation method thereof, specifically using L-phenylalanine as a raw material to prepare a new type of chiral selector 2-(2 -Hydroxy-3-alkoxy) propyl group-(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, which is then coated on the bonded stationary phase of reversed-phase chromatography; It can realize the direct separation of amino acid samples; its disadvantages are: the separation takes a long time, and the tailing of the effluent components is serious; compared with the bonded stationary phase, the coated stationary phase is easy to lose, limit its useful life

Synthesis of two kinds of L-proline silica gel bonded chiral ligand exchange stationary phases with different bonding amounts (Zhu Xinyi, Han Xiaoqian et al. "Chromatography", 2002, 20(3): 223-226), using ligand exchange Chromatography separates a series of amino acids, and the results show that the resolution ability of immobilized relative amino acids with different bonding amounts is quite different; it only resolves a limited number of amino acids, and it takes a long time, and the final components are separated. severe tail

Synthesis of 2-(2-hydroxy-3-alkoxy)propyl-(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid chiral selector (Wang Qunbiao, Long Yuande et al. "Chromatography", 2000, 18 (2): 112-114), prepared two novel coating chiral ligand exchange chromatographic stationary phases, and resolved several amino acids; long analysis time

[0004] In the above related research literature, the stationary phases prepared by different methods (most of the amino acids used are proline and hydroxyproline) generally take a long time to separate DL-amino acids (the back-flowing components Severe tailing), or need to be separated at a higher temperature, which not only makes the operation complicated, but also greatly affects the service life of the chromatographic column

Images