Method of fust preparing linkage type polysaccharide chiral fixed phase

A chiral stationary phase and polysaccharide technology, applied in the field of chromatography preparation, can solve the problems of unrealized commercial production, numerous reaction steps, cumbersome operation, etc., and achieve the effects of easy operation, wide application range, and simple production process

Inactive Publication Date: 2005-06-08
萍乡分水科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Functional groups with polymerization properties are introduced into polysaccharide molecules under the action of light (document 3. Photochemically cross-linked polysaccharide derivatives as supports for the chromatographic separation of enantiomers; E.Francotte, PCT WO 96 / 27615 (1996).), through photopolymerization The stationary phase is prepared by the action, the process is complicated and the operation is cumbersome
Tatsumi Murakami et al. (Document 4. Separating agent for optical isomers, its preparation method and application; Tatsumi Murakami, Akito Ichida, 94190414 (1994)) through the hydroxyl on the 6-position of polysaccharide derivatives, using two Isocyanate difunctional reagent, cross-linking polysaccharide derivatives to the surface of silica gel, is a selective immobilization method, with many reaction steps and long time
[0003] Therefore, the chemically bonded polysaccharide chiral stationary phase has not yet been commercially produced, and it is urgent to develop a fast and simple chemical bonding method.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Take 1g of cellulose, put it into a reactor containing 30mL of pyridine, slowly add 5mL of phenyl isocyanate and 0.3mL of γ-isocyanate propyl triethoxysilane under the condition of electromagnetic stirring, and the temperature of the reaction system is raised to about 90 ℃, react for 10 hours, after the reaction system is cooled to room temperature, pour the reaction liquid into a beaker containing a large amount of methanol, precipitate out, centrifuge the precipitate, collect the solid, and dry to obtain triethoxy-containing Cellulose phenyl carbamate derivatives;

[0018] Coat the prepared derivative on the surface of silica gel (5 μ, 200 Å) at a ratio of 40% (w / w), place it in a 50 mL round bottom flask, add 10 mL of toluene and 2 mL of pyridine, and react at 80 ° C 5 hours. After cooling, the product was thoroughly washed with tetrahydrofuran and methanol, and dried in vacuum to obtain a bonded cellulose phenyl carbamate chiral stationary phase.

Embodiment 2

[0020] The difference from Example 1 is that 3 g of cellulose is placed in 100 mL of pyridine, a sufficient amount of 10 mL of 3,5-dimethylphenyl isocyanate and 0.9 mL of triethoxyaminopropyl isocyanate silane are added, At 90-95°C, react for about 10 hours to obtain triethoxycellulose phenyl carbamate derivatives.

[0021] It is better to control the reaction ratio between triethoxyaminopropylisocyanate silane and polysaccharide derivatization reagent, generally 1:15 (v / v).

[0022] The present invention adopts a non-selective chemical bonding method, that is, the polysaccharide derivative is fixed on the chromatographic carrier through any hydroxyl group at the 2-, 3-, or 6-position of the glucose unit. The present invention can also adopt the method of selective chemical bonding, that is, the polysaccharide derivative is fixed on the surface of the chromatographic substrate only through the hydroxyl group at the 6-position of the glucose unit. There is no obvious differenc...

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Abstract

A method for synthesis of linking polysaccharide chiral stationary phase, includes the following steps: 1) in the reactor with organic solvent, polysaccharide and derivative solvent of polysaccharide react with including functional group which can react with polysaccharide hydrocarbon radical, then though centrifugal separation the solid substance is collected; 2) coat the prepared polysaccharide derivative containing trihydroxyme or on the surface of silica gel matrixof chromatogram filler, then they are mixed with toluene and pyridine in reactor , cooled after reaction, then use tetrahydrofuran and carbinol separately to wash the creature, which are dried in vacuum, acquiring the linking polysaccharide chiral stationary phase. Its advantages are: wide field of use, simple and rapid preparation.

Description

technical field [0001] The invention relates to the preparation of chromatography, in particular to a method for rapidly preparing bonded polysaccharide chiral stationary phase. Background technique [0002] Polysaccharide chiral stationary phases show great advantages in the separation and preparation of chiral enantiomers, and have very broad application prospects. At present, the commercialized polysaccharide derivative stationary phase adopts the method of physical coating to immobilize the polysaccharide derivative on the chromatographic matrix, so there is a problem of chiral selective agent loss, and the components of the mobile phase are affected in practical applications. Larger restrictions. Due to this disadvantage, some enantiomers have very low solubility or even insolubility under suitable mobile phase conditions on such stationary phases, thus limiting their use in chiral separation applications. The preparation of polysaccharide chiral stationary phase by c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
Inventor 邹汉法陈小明秦峰刘月启
Owner 萍乡分水科技有限公司
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