Novel chiral chromatographic column fixed phase and preparation method thereof

A chiral stationary phase, chiral technology, applied in chemical instruments and methods, other chemical processes, etc., can solve the problem of serious tailing of eluted components, easy loss of coated stationary phase, and poor stability of stationary phase. and other problems, to achieve the effect of simple and easy method, low cost and good binding force

Inactive Publication Date: 2011-09-07
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the prior art, the Chinese patent No. 99117305.8 discloses a chiral ligand exchange chromatography stationary phase and its preparation method, specifically using L-phenylalanine as a raw material to prepare a new type of chiral selector 2 -(2-Hydroxy-3-alkoxy)propyl-(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, which was then coated on reversed-phase On the other hand, the direct separation of amino acid samples can be realized; the disadvantage of this technical scheme is that the separation takes a long time, and the tailing of the effluent components is serious. Compared with the bonded stationary phase, the coating type Stationary phase is prone to loss, limiting its useful life
[0006] The Chinese Invention Application Publication No. 200410021198.8 discloses a chemically bonded chiral stationary phase and its preparation method. The specific method is to use a glycopeptide macrocyclic antibiotic-norvancomycin as a chiral selector, and through chemical bonding Bonding it to a carrier can separate many different types of chiral drugs. The disadvantages are that the column efficiency is not high and the stability of the stationary phase is not good.

Method used

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  • Novel chiral chromatographic column fixed phase and preparation method thereof
  • Novel chiral chromatographic column fixed phase and preparation method thereof
  • Novel chiral chromatographic column fixed phase and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1. Pretreatment of the carrier: Take 1.0g of silica gel balls, put them into a round bottom flask, then add an appropriate amount of concentrated hydrochloric acid, heat to reflux for 2 hours, cool down, filter, wash the solid with water to pH=7, rinse the solid with acetone and ether in turn, and drain it spare.

[0029] 2. L-ValCONH (CH 2 ) 17 CH 3 synthesis:

[0030] 1) Synthesis of Z-L-ValCOOH

[0031] After reacting 0.5 mol of L-ValCOOH with 0.5 mol of benzyloxychloride and 0.5 mol of NaOH in an ice-water bath for 12 hours, Z-L-ValCOOH was obtained after extraction, acidification, dehydration, recrystallization and drying.

[0032] 2) Z-L-ValCONH (CH 2 ) 17 CH 3 Synthesis

[0033] Weigh 0.2 mol of Z-L-ValCOOH in a three-necked flask, add 500 mL of ethyl acetate, heat and stir to dissolve. Add 0.2 mol of DCC, stir for 1 hour, add 0.2 mol of triethylamine, weigh 0.2 mol of octadecylamine and dissolve it in 100 ml of chloroform, add it to the mixture, and sti...

Embodiment 2

[0040]1. Pretreatment of the carrier: Take 1.0g of silica gel balls, put them into a round bottom flask, then add an appropriate amount of concentrated hydrochloric acid, heat to reflux for 2 hours, cool down, filter, wash the solid with water to pH=7, rinse the solid with acetone and ether in turn, and drain it spare.

[0041] 2. D-ValCONH (CH 2 ) 17 CH 3 synthesis

[0042] 1) Synthesis of Z-D-ValCOOH

[0043] React 0.5 mol of D-ValCOOH with 0.5 mol of benzyloxychloride and 0.5 mol of NaOH in an ice-water bath for 12 hours, then extract, acidify, remove water, recrystallize, and dry to obtain Z-D-ValCOOH.

[0044] 2) Z-D-ValCONH (CH 2 ) 17 CH 3 Synthesis

[0045] Weigh 0.2 mol of Z-D-ValCOOH in a three-necked flask, heat and stir 500 mL of ethyl acetate to dissolve. Add 0.2 mol of DCC, stir for 1 hour, add 0.2 mol of triethylamine, weigh 0.2 mol of octadecylamine and dissolve it in 100 ml of chloroform, add it to the mixture, and stir in an ice bath for 2 hours. Sti...

Embodiment 3

[0052] 1. Pretreatment of the carrier: Take 1.0g of silica gel balls, put them into a round-bottomed flask, then add an appropriate amount of concentrated hydrochloric acid, heat to reflux for 2 hours, cool down, filter, wash the solid with water to pH=7, wash the solid with acetone and ether in turn, and then pump Dry.

[0053] 2. L-PheCONH (CH 2 ) 17 CH 3 synthesis

[0054] 1) Synthesis of Z-L-PheCOOH

[0055] After reacting 0.5 mol of L-PheCOOH with 0.5 mol of benzyloxychloride and 0.5 mol of NaOH in an ice-water bath for 12 hours, Z-L-PheCOOH was obtained after extraction, acidification, dehydration, recrystallization, and drying.

[0056] 2) Z-L-PheCONH (CH 2 ) 17 CH 3 Synthesis

[0057] Weigh 0.2 mol of Z-D-PheCOOH in a three-necked flask, heat and stir 500 mL of ethyl acetate to dissolve. Add 0.2 mol of DCC, stir for 1 hour, then add 0.2 mol of triethylamine, weigh 0.2 mol of octadecylamine and dissolve in 100 ml of chloroform, add to the mixture, and stir in i...

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Abstract

The invention belongs to the field of chiral fixed phases and relates to a chiral chromatographic column fixed phase in which an amino acid derivative is taken as a matrix of a chiral selective agent and the amino acid derivative is modified onto the surface of a carrier with a chemical bonding method. The chiral fixed phase consists of a chiral monomer and a carrier, wherein the general structure of the chiral monomer is shown in the specifications, wherein m is any integer from 1 to 17; n is any integer from 1 to 10; R is an amino acid side chain group; and the carrier is silica gel. The chiral selective agent is modified on the surface of the carrier by taking amino acid as the matrix with a bonding method, so that the bonding force between the chiral selective agent and the carrier isgood, and the obtained chiral chromatographic column fixed phase has stable chemical property, a good separation effect and high column efficiency, is convenient to use, and is prevented from tailing.

Description

technical field [0001] The invention belongs to the field of chiral stationary phases, and relates to a chiral chromatographic column stationary phase which uses amino acid derivatives as the matrix of chiral selectors and modifies the amino acid derivatives on the surface of carriers by chemical bonding. Background technique [0002] Chirality is one of the essential properties of nature on which human beings depend. The chemical processes in life phenomena are carried out in a highly asymmetric environment. Biological macromolecules such as proteins, polysaccharides, nucleic acids, etc., all have chirality, and they create a chiral environment in the organism. Proteins except bacteria are composed of left-handed L-amino acids; sugars in polysaccharides and nucleic acids are right-handed D-configurations. [0003] About half of the western medicines currently on the market contain chiral centers, and about half of them are sold in the form of racemates. It was not until t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/29B01J20/30
Inventor 杨永刚李艺李宝宗薛珍
Owner SUZHOU UNIV
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