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Method for preparing D-p-methylsulfonyl phenyl serine ethyl ester through immobilized enzyme catalysis

A technology of thiamphenylphenylserine ethyl ester and immobilized enzymes, applied to biochemical equipment and methods, and enzymes immobilized on or in inorganic carriers, can solve the problems of complicated synthesis process and easy inactivation of enzymes, etc. Achieve the effects of high selectivity, improved utilization, and mild reaction conditions

Active Publication Date: 2021-06-04
APELOA PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis process of lipase is relatively complicated and the enzyme is easily inactivated under some complex reaction conditions.

Method used

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  • Method for preparing D-p-methylsulfonyl phenyl serine ethyl ester through immobilized enzyme catalysis
  • Method for preparing D-p-methylsulfonyl phenyl serine ethyl ester through immobilized enzyme catalysis
  • Method for preparing D-p-methylsulfonyl phenyl serine ethyl ester through immobilized enzyme catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 1) Superparamagnetic Fe 3 o 4 Enzymes immobilized on nanoparticles (Fe 3 o 4 Preparation of @PEI-Lipase)

[0035] 6.48g of ferric chloride hexahydrate, 4.704g of sodium citrate and 9.84g of sodium acetate were dissolved in 400mL of ethylene glycol, and after the mixture was dispersed evenly by ultrasonic waves, it was distributed into ten 100mL polytetrafluoroethylene autoclaves. React at 140°C for 12 hours. After cooling down to room temperature, the crude product is separated by a magnet and washed with water and ethanol for 3-5 times (to neutrality). Vacuum dried for later use.

[0036] Above-mentioned magnetic nanoparticles 5g and PEI (M w =10000) 25g was dissolved in 60mL of distilled water, and the reaction solution was vigorously stirred for 24 hours, then magnetically separated. The solid was washed 3-4 times with distilled water (20mL) and dried in vacuum for subsequent use (marked as Fe 3 o 4 @PEI).

[0037] The aforementioned PEI-activated magnetic n...

Embodiment 2

[0046] 1) Superparamagnetic Fe 3 o 4 Enzymes immobilized on nanoparticles (Fe 3 o 4 Preparation of @PEI-Lipase)

[0047] 6.48g of ferric chloride hexahydrate, 4.704g of sodium citrate and 9.84g of sodium acetate were dissolved in 400mL of ethylene glycol. After the mixture was dispersed evenly by ultrasonic, it was distributed into ten 100mL polytetrafluoroethylene autoclaves. React at 200°C for 6 hours. After cooling down to room temperature, the crude product is separated by a magnet and washed with water and ethanol for 3-5 times (to neutrality). Vacuum dried for later use.

[0048] 5 g of the above-mentioned magnetic nanoparticles and 25 g of PEI were dissolved in 60 mL of distilled water, and the reaction was vigorously stirred for 24 hours before magnetic separation. The solid was washed 3-4 times with distilled water (20mL) and dried in vacuum for subsequent use (marked as Fe 3 o 4 @PEI).

[0049] Activation and the immobilization of enzyme are the same as embod...

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Abstract

The invention discloses a method for preparing D-p-methylsulfonyl phenyl serine ethyl ester through immobilized enzyme catalysis. The method is mild in condition and simple in post-treatment, enzymes can be recycled, and the corrosivity to a production device is low. The method for preparing the D-p-methylsulfonyl phenyl serine ethyl ester with high optical purity through a superparamagnetic Fe3O4 nanoparticle immobilized novel lipase asymmetric catalytic resolution system has the advantages that the total yield of the D-p-methylsulfonyl phenyl serine ethyl ester with the optical purity reaches 85%, the enantiomeric excess (ee%) of the obtained product reaches 93%, and the higher yield and optical purity are achieved; and in addition, post-treatment is simple, an immobilized enzyme catalyst can be recycled through a simple external magnetic field, and after the immobilized enzyme catalyst is repeatedly used for 10 times, the product still has the high yield and ee value.

Description

technical field [0001] The present invention relates to a preparation method of D-p-thymphenylphenylserine ethyl ester, in particular to a new type of lipase-CuCl immobilized by magnetic nanoparticles 2 Asymmetric catalytic resolution method for preparing D-p-thymphenylphenylserine ethyl ester with high optical purity. Background technique [0002] Chiral compounds are widely found in various components such as drug molecules, natural products, and bioactive molecules. In particular, in the field of medicinal chemistry, different chiralities of drugs usually show different drug activities and toxicity, the most famous being the "reactin event" that occurred in the 1950s and 1960s. Therefore, in pharmaceutical engineering, the production of pharmaceutical intermediates with qualified optically pure properties has become necessary and increasingly important. D-p-methylsulfone phenylserine ethyl ester (D-p-MPSE) is an important intermediate in the synthesis of the antibiotic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P7/62C12N11/14
CPCC12P41/001C12P41/005C12P7/62C12N11/14C12N9/20C12Y301/01003Y02P20/584
Inventor 金毅强申屠有德雷江徐健
Owner APELOA PHARM CO LTD
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