Synthesis and application of L-phenylalanine derived Beta-cyclodextrin bonded silica gel for separating alanine enantiomer

A technology of phenylalanine and bonded silica gel, which is applied in the field of analytical chemistry to achieve simple operation, low cost and good adsorption effect

Inactive Publication Date: 2013-07-10
JIANGSU UNIV
View PDF1 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] β-cyclodextrin-bonded silica gel and its derivatives have obvious advantages in chiral separation, while using L-phenylalanine-modified β-cyclodextrin-bonded silica gel and applying it to alanine and other chiral separations The separation of sex enantiomers has not been reported publicly

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) L-phenylalanine derived β-cyclodextrin bonded silica gel (L-Phe-CD / SiO 2 ) synthesis: Weigh 0.5 g of dried L-phenylalanine and tosylated β-cyclodextrin bonded silica gel (TsCD / SiO 2 ) 1g was placed in 60mL of anhydrous pyridine, stirred and reacted at 70°C for 40h in a nitrogen atmosphere; Afterwards, it was vacuum-dried at 100 °C for 3 h to obtain it.

[0039] (2) Separation of alanine enantiomers: take equal masses of L-alanine (L-Ala) and D-alanine (D-Ala), mix them and dissolve them in water to obtain the exosome of alanine racemic solution; glass tubes capped at the bottom filled with L-phenylalanine-derived β-cyclodextrin-bonded silica gel (L-Phe-CD / SiO 2 ), add a certain volume of alanine racemic solution, seal it, and put it in a 25°C constant temperature water tank until the adsorption reaches equilibrium; after the adsorption is completed, centrifuge and use a UV-2450 spectrophotometer to measure the clear The absorbance of the solution was measured wit...

Embodiment 2

[0041] (1) L-phenylalanine derived β-cyclodextrin bonded silica gel (L-Phe-CD / SiO 2 ) synthesis: Weigh 1 g of dried L-phenylalanine and p-toluenesulfonylated β-cyclodextrin bonded silica gel (TsCD / SiO 2 ) 1g was placed in 50mL of anhydrous pyridine, stirred and reacted at 70°C for 52h in a nitrogen atmosphere; Afterwards, it was vacuum-dried at 120 °C for 5 h to obtain it.

[0042] (2) Separation of alanine enantiomers: take equal masses of L-alanine (L-Ala) and D-alanine (D-Ala), mix them and dissolve them in water to obtain the exosome of alanine racemic solution; glass tubes capped at the bottom filled with L-phenylalanine-derived β-cyclodextrin-bonded silica gel (L-Phe-CD / SiO 2 ), add a certain volume of alanine racemic solution, seal it, and put it in a constant temperature water tank at 30°C until the adsorption reaches equilibrium; after the adsorption is completed, centrifuge and use a UV-2450 spectrophotometer to measure the clear The absorbance of the solution was...

Embodiment 3

[0044] (1) L-phenylalanine derived β-cyclodextrin bonded silica gel (L-Phe-CD / SiO 2 ) synthesis: Weigh 2 g of dried L-phenylalanine and tosylated β-cyclodextrin bonded silica gel (TsCD / SiO 2 ) 1 g in 40 mL of anhydrous pyridine, stirred and reacted at 70 °C for 40 h in a nitrogen atmosphere; the reaction liquid was removed by suction filtration, and the product was washed with anhydrous pyridine, methanol, ether, absolute ethanol, methanol, distilled water, acetone in turn, and suction filtered Afterwards, it was vacuum-dried at 130 °C for 5 h to obtain it.

[0045] (2) Separation of alanine enantiomers: take equal masses of L-alanine (L-Ala) and D-alanine (D-Ala), mix them and dissolve them in water to obtain the exosome of alanine racemic solution; glass tubes capped at the bottom filled with L-phenylalanine-derived β-cyclodextrin-bonded silica gel (L-Phe-CD / SiO 2 ), add a certain volume of alanine racemic solution, seal it, and put it in a 45°C constant temperature water ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
particle diameteraaaaaaaaaa
Login to view more

Abstract

The invention belongs to the field of analytic chemistry, relates to synthesis of a chiral column material, and in particular relates to synthesis and an application of L-phenylalanine derived Beta-cyclodextrin bonded silica gel for separating an alanine enantiomer. According to the technical scheme, the synthesis process comprises the following steps: firstly, preparing activated silica gel; then synthesizing Beta-cyclodextrin bonded silica gel; next, synthesizing tosylated Beta-cyclodextrin bonded silica gel; and finally, derivatizing an obtained product by using L-phenylalanine. The prepared L-phenylalanine derived Beta-cyclodextrin bonded silica gel is yellow solid powder which is insoluble in water and organic solvents such as N,N-dimethyl formamide and the like as well as difficult to dissolve in acid solutions. If the synthesized L-phenylalanine derived Beta-cyclodextrin bonded silica gel is served as a chromatographic filling material to perform adsorption separation on an aqueous solution containing the alanine enantiomer at the constant temperature and under the normal pressure, the good chiral separation effect can be achieved. When the L-phenylalanine derived Beta-cyclodextrin bonded silica gel is used for separating the alanine enantiomer, the operation is simple, the cost is low and the adsorption effect is good. Therefore, the L-phenylalanine derived Beta-cyclodextrin bonded silica gel has a definite practical value.

Description

technical field [0001] The invention belongs to the field of analytical chemistry, and relates to the synthesis of a chiral column material, in particular to the synthesis of an L-phenylalanine-derived β-cyclodextrin bonded silica gel and its application to the separation of alanine enantiomers . Background technique [0002] The chirality of compounds is very common, and it has attracted widespread attention in medicine, pesticides and life chemistry. In view of the special relationship between the three-dimensional structure of organic molecules and their biological activity, the establishment of a high-specificity, high-resolution enantioresolution and determination method will have important theoretical and theoretical implications for improving molecular activity, reducing side effects, and in-depth research on the mechanism of action. practical significance. [0003] The chiral stationary phase is made of optically active monomers fixed on silica gel or other polymer...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16B01J20/29C07C227/34C07C229/08
Inventor 邱凤仙贺凯晨杨冬亚秦佼
Owner JIANGSU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap