Application of Beta-cyclodextrin derivatives in preparing gas chromatography chiral stationary phases

A chiral stationary phase and gas chromatography technology are applied in the application field of preparing gas chromatography chiral stationary phases to achieve the effect of excellent separation ability

Inactive Publication Date: 2012-10-31
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] At present, there is no cyclodextrin derivative as a chiral stationary phase for capillary gas chromatography, which can meet the needs of all enantiomeric separations in practical work

Method used

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  • Application of Beta-cyclodextrin derivatives in preparing gas chromatography chiral stationary phases
  • Application of Beta-cyclodextrin derivatives in preparing gas chromatography chiral stationary phases
  • Application of Beta-cyclodextrin derivatives in preparing gas chromatography chiral stationary phases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Preparation of 2,3,6-tri-O-pentanoyl-β-cyclodextrin

[0033] Dissolve 0.3g (0.264mmol) of β-cyclodextrin in 15mL of dry chloroform, add 2.5mL of pyridine at 0°C, add 2.5mL of valeryl chloride (21.06mmol) dropwise under ice-cooling, and stir at 0°C for 0.5h. The reaction was stirred at 60°C for 6h. After the reaction was completed, the solvent was removed under reduced pressure, dissolved in 20 mL of ice water, extracted three times with 20 mL of chloroform, the chloroform layers were combined, washed twice with saturated aqueous sodium bicarbonate solution, then washed twice with water, and finally dried over anhydrous sodium sulfate , concentrated under reduced pressure to obtain a crude product. Purification by column chromatography (toluene / ethyl acetate=1:1, v / v) gave a brown viscous product (yield 20%).

[0034] The structural confirmation data are as follows:

[0035] IR (cm -1 ): 2958, 2930, 2872 (CH 2 , CH 3 ), 1740 (C=O), 1462, 1380, 1343, (CH ...

Embodiment 2

[0038] Example 2: Evaluation of β-cyclodextrin derivatives as chiral stationary phases in capillary gas chromatography

[0039] Evaluation was performed by capillary gas chromatography. The prepared 2,3,6-tri-O-pentanoyl-β-cyclodextrin was used as the chiral stationary phase, and after being dissolved in dichloromethane, the stationary phase wall was coated with NaCl by the traditional static method. The inner wall of the roughened quartz capillary column was prepared to prepare a chiral capillary column for gas chromatography, and the dead time was determined by methane. The evaluation results can be seen in Table 1 and Figure 1-4 .

[0040] Table 1 2,3,6-tri-O-pentanoyl-β-cyclodextrin chiral stationary phase resolution results of some enantiomer samples

[0041]

[0042] High-purity N for carrier gas 2 (99.99%); gasification chamber temperature: 250°C; hydrogen flame ionization detector temperature: 280°C; split ratio: 30:1.

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Abstract

The invention discloses a novel application of Beta-cyclodextrin derivatives. According to the invention, the structural formula of the Beta-cyclodextrin derivatives is shown as Formula I, wherein R has the following structure: n is 1 to 10. The novel application of Beta-cyclodextrin derivatives reforms to the application in preparing gas chromatography chiral stationary phases. The Beta-cyclodextrin derivatives shown in the Formula I are taken as gas chromatography chiral stationary phases, so that certain isomers can be successfully separated, and the Beta-cyclodextrin derivatives have excellent separation capacity in separating 2-chlorine methyl propionate isomers and pantothenic acid lactone isomers. (Formula I).

Description

technical field [0001] The invention relates to the application of beta cyclodextrin derivatives in the preparation of gas chromatography chiral stationary phase. Background technique [0002] Chirality is one of the essential attributes of nature that human beings depend on for survival. Biological macromolecules such as proteins, polysaccharides, and nucleic acids all have chirality. Optically active chiral substances widely exist in animals and plants. Studies have found that different enantiomers of medicines and pesticides with chiral centers have different biological activities, and some enantiomers even have toxic side effects. Therefore, obtaining optically pure medicines, pesticides, spices, flavors, food additives, new materials, etc. has become a research hotspot in the corresponding field, while identifying the absolute configuration of chiral compounds, determining their optical purity, and studying simple and convenient pairs Enantiomer analysis method has th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/29C08B37/16
Inventor 史雪岩高希武梁沛宋敦伦
Owner CHINA AGRI UNIV
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