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Synthesis of L-tryptophan derived beta-cyclodextrin bonded silica gel and application thereof for separating alanine enantiomers

A technology of bonding silica gel and cyclodextrin, applied in the field of analytical chemistry, to achieve low cost, good chiral separation effect, and good adsorption effect

Inactive Publication Date: 2015-04-22
JIANGSU UNIV
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  • 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, and β-cyclodextrin-bonded silica gel modified with L-tryptophan and applied to alanine and other chiral separations The separation of enantiomers has not been reported publicly

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) L-tryptophan-derived β-cyclodextrin bonded silica gel (L-Trp-CD / SiO 2 ) Synthesis: Weigh 0.5 g of dried L-tryptophan and p-toluenesulfonylated β-cyclodextrin bonded silica gel (TsCD / SiO 2 ) 1g was placed in 50mL of anhydrous pyridine, stirred at 70℃ for 40h in a nitrogen atmosphere; the reaction solution was removed by suction filtration, and the product was washed with anhydrous pyridine, methanol, ether, absolute ethanol, methanol, distilled water, acetone, and suction filtered Then, vacuum drying at 120 ℃ for 4 h, it is obtained.

[0039] (2) Separation of alanine enantiomers: take the same mass of L-alanine (L-Ala) and D-alanine (D-Ala), mix them and dissolve them in water to obtain the outer Racemic solution; fill the glass tube with the end capped at the bottom with L-tryptophan-derived β-cyclodextrin-bonded silica gel (L-Trp-CD / SiO 2 ), add a certain volume of alanine racemic solution, seal it, and put it in a constant temperature water tank at 25°C until the ad...

Embodiment 2

[0041] (1) L-tryptophan-derived β-cyclodextrin bonded silica gel (L-Trp-CD / SiO 2 ) Synthesis: Weigh 1g of dried L-tryptophan and p-toluenesulfonylated β-cyclodextrin bonded silica gel (TsCD / SiO 2 ) 1g was placed in 50mL of anhydrous pyridine, stirred at 70°C for 40h in a nitrogen atmosphere; the reaction solution was removed by suction filtration, and the product was washed with anhydrous pyridine, methanol, ether, absolute ethanol, methanol, distilled water, acetone, and suction filtered Then, vacuum drying at 120 ℃ for 4 h, it is obtained.

[0042] (2) Separation of alanine enantiomers: take the same mass of L-alanine (L-Ala) and D-alanine (D-Ala), mix them and dissolve them in water to obtain the outer Racemic solution; fill the glass tube with the end capped at the bottom with L-tryptophan-derived β-cyclodextrin-bonded silica gel (L-Trp-CD / SiO 2 ), add a certain volume of alanine racemic solution, seal it, put it in a 30℃ constant temperature water tank, until the adsorption ...

Embodiment 3

[0044] (1) L-tryptophan-derived β-cyclodextrin bonded silica gel (L-Trp-CD / SiO 2 ) Synthesis: Weigh 2.5g of dried L-tryptophan and p-toluenesulfonylated β-cyclodextrin bonded silica gel (TsCD / SiO 2 ) 1g was placed in 50mL of anhydrous pyridine, stirred at 80℃ for 40h in a nitrogen atmosphere; the reaction solution was removed by suction filtration, and the product was washed with anhydrous pyridine, methanol, ether, absolute ethanol, methanol, distilled water, acetone, and suction filtered Then, vacuum drying at 120 ℃ for 4 h, it is obtained.

[0045] (2) Separation of alanine enantiomers: take the same mass of L-alanine (L-Ala) and D-alanine (D-Ala), mix them and dissolve them in water to obtain the outer Racemic solution; fill the glass tube with the end capped at the bottom with L-tryptophan-derived β-cyclodextrin-bonded silica gel (L-Trp-CD / SiO 2 ), add a certain volume of alanine racemic solution, seal it, and put it in a 45℃ constant temperature water tank until the adsorpt...

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Abstract

The invention belongs to the field of analytical chemistry and relates to synthesis of a chiral column material, in particular to synthesis of L-tryptophan derived beta-cyclodextrin bonded silica gel and application thereof for separating alanine enantiomers. The technical scheme of the invention is as follows: activated silica gel is prepared firstly, then beta-cyclodextrin bonded silica gel is synthetized, furthermore, tosylation beta-cyclodextrin bonded silica gel is synthetized, and finally L-tryptophan derivatization is performed, so that a product is obtained. The synthetized L-tryptophan derived beta-cyclodextrin bonded silica gel is light yellow solid powder which is insoluble in water or in organic solvents of N, N'-dimethyl formamide and the like and is difficult to solute in an acid solution or an alkaline solution. The synthetized L-tryptophan derived beta-cyclodextrin bonded silica gel is used as a chromatograph filling material, under the constant temperature and pressure, a water solution containing alanine enantiomers is adsorbed and separated, and a good chiral separation effect is achieved. The material is used for separating the alanine enantiomers, the operation is simple, the cost is low, the adsorption effect is good, and a certain practical value is achieved.

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-tryptophan-derived β-cyclodextrin bonded silica gel and its application to the separation of alanine enantiomers. Background technique [0002] The property that a substance and its mirror image cannot superimpose is called chirality. Chirality is a common feature in nature. Many macromolecules related to life activities, such as proteins, polysaccharides, nucleic acids, etc., have chirality. Research and application value. In order to study the relationship between different enantiomeric structures and activities, monitor the stereoselective synthesis process of chiral compounds, evaluate the optical purity of chiral compounds, etc., it is particularly important to study the resolution methods of chiral compounds. [0003] Cyclodextrin derivative stationary phase, this type of stationary phase i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J20/29B01J20/30B01D15/08
Inventor 邱凤仙贺凯晨杨冬亚秦佼
Owner JIANGSU UNIV
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