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A kind of preparation method of α-cholesteryl glutamate gel

A technology of cholesteryl ester and glutamic acid, which is applied in the directions of gel preparation, organic chemistry method, chemical instrument and method, etc., can solve the problems of long reaction time, difficult reaction and low yield, etc.

Active Publication Date: 2019-06-11
TAIYUAN UNIV OF TECH
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AI Technical Summary

Problems solved by technology

What is reported in the literature is to directly use the carboxyl of amino acid and cholesterol to carry out esterification reaction to prepare different amino acid cholesteryl esters. Due to the mutual influence of amino and carboxyl groups of amino acids in this method, the reaction is difficult to carry out, the reaction time is long and the product complex, difficult to separate, and low yield; if a method can be found to protect and activate the carboxyl group of the amino acid amino acid, the reaction can be directed, the reaction time can be shortened, and the yield can be increased. The rigid skeleton of the carboxyl group and cholesterol increases the performance of the gel, expands the application range of cholesterol, and provides a powerful means for similar reactions

Method used

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  • A kind of preparation method of α-cholesteryl glutamate gel
  • A kind of preparation method of α-cholesteryl glutamate gel
  • A kind of preparation method of α-cholesteryl glutamate gel

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preparation example Construction

[0020] Concrete preparation method steps are as follows:

[0021] Step 1. Weigh 2-5g of α-glutamic acid and mix it with acid anhydride with a mass ratio of 1:1, heat and melt, then add 5-10ml of acetic anhydride, reflux at 120-140°C for 10-30min, and let stand after the reaction , cooled to room temperature, precipitated crystals, filtered, washed the crystals three times with ethyl acetate, and dried in vacuum at 60°C to obtain α-amino-protected glutamic anhydride.

[0022] Step 2, add cholesterol to the product prepared above according to its molar ratio of 1:1-3:1, add 60ml of dichloromethane to fully dissolve and dissolve, add catalyst 0.5-1.2g dicyclohexylcarbodiimide (DCC), 2-4ml of pyridine was stirred at room temperature for 4 hours, filtered, and the filter residue was discarded. The filtrate was washed with 0.01mol / L hydrochloric acid, 0.01mol / L sodium hydroxide and deionized water to neutrality, and rotary evaporated, and the obtained solid was washed with hot metha...

Embodiment 1

[0036] (1) Weigh 2g of α-glutamic acid and mix it with succinic anhydride with a mass ratio of 1:1, heat and melt, then add 5ml of acetic anhydride, reflux at 120°C for 30min, let stand after the reaction, cool to room temperature, and precipitate The crystals were filtered, washed three times with ethyl acetate, and dried under vacuum at 60°C to obtain α-amino-protected glutamic anhydride.

[0037] (2) Add cholesterol to the product prepared above at a molar ratio of 2:1, add 60ml of dichloromethane to fully dissolve, add catalyst 0.5g DCC, 3ml of pyridine, stir at room temperature for 4h, filter, and discard the filter residue. The filtrate was washed with 0.01mol / L of hydrochloric acid, 0.01mol / L of sodium hydroxide and deionized water to neutrality, and then evaporated by rotary evaporation. The resulting solid was washed three times with hot methanol, and the crude product was separated and purified by silica gel chromatography (ethyl acetate Esters: cyclohexane = 1:4) to...

Embodiment 2

[0040](1) Weigh 5g of α-glutamic acid and mix it with phthalic anhydride with a mass ratio of 1:1, heat and melt, then add 10ml of acetic anhydride, reflux at 140°C for 20min, let stand after the reaction, and cool to room temperature , precipitated crystals, filtered, washed the crystals with ethyl acetate three times, and dried in vacuum at 60°C to obtain α-amino-protected glutamic anhydride.

[0041] (2) Add cholesterol to the product prepared above at a molar ratio of 3:1, add 60ml of dichloromethane to fully dissolve, add catalyst 1.2g of DCC, 4ml of pyridine, stir at room temperature for 4h, filter, and discard the filter residue. The filtrate was washed with 0.01mol / L of hydrochloric acid, 0.01mol / L of sodium hydroxide and deionized water to neutrality, and then evaporated by rotary evaporation. The resulting solid was washed three times with hot methanol, and the crude product was separated and purified by silica gel chromatography (ethyl acetate Esters: cyclohexane = ...

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Abstract

The invention relates to a preparation method of cholesteryl alpha-glutamate gel. According to the method, the reaction of acid anhydride and alpha-glutamic acid is used for protecting alpha-amino, the intramolecular dehydration is performed to form cyclic glutamate anhydride, then the cyclic glutamate anhydride has esterification reaction with cholesterol to generate alpha-amino protected cholesteryl glutamate, and then hydrazine hydrate is used to remove the protection group anhydride to synthesize the cholesteryl alpha-glutamate. The cholesteryl alpha-glutamate gel prepared by using the method can overcome the problems that the reaction condition for preparing the cholesteryl alpha-glutamate gel by virtue of direct esterification is not easy to control and the yield is low; the gel prepared by the method can effectively improve the biocompatibility and gelling property, and a useful means is provided for preparing a drug carrier and a sensor material.

Description

technical field [0001] The present invention relates to a preparation method of cholesterol-based gel, especially first using acid anhydride to react with α-glutamic acid to protect its α-amino group, and at the same time carry out intramolecular dehydration to form cyclic glutamic anhydride, and then carry out esterification with cholesterol The reaction generates α-amino-protected cholesteryl glutamate, and then uses hydrazine hydrate to remove the protective group to synthesize α-cholesteryl glutamate. Background technique [0002] Small molecule gels have good thermal reversibility, and are usually used for induction or stimuli responsiveness by heating, ultrasound, and photoelectricity. Therefore, it has good application prospects in drug loading, sensor preparation, and inorganic nanomaterial preparation. Amino acid cholesteryl ester is prepared by the esterification reaction of amino acid with strong biocompatibility and cholesterol. Because of its rigid skeleton, mu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J43/00C07J41/00B01J13/00
CPCB01J13/0052C07B2200/07C07J41/0055C07J41/0088C07J43/003
Inventor 靳利娥张青兰巴丽思靳文博曹青
Owner TAIYUAN UNIV OF TECH
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