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Preparation methods of immobilized nitrile group hydratase and (S)-N-ethylpyrrolidine-2-formamide

A technology for hydration of ethylpyrrolidine and nitrile group, applied in the field of biomedicine, can solve the problems of expensive chiral raw materials and chiral catalysts, low atom utilization rate of chemical resolution method, asymmetric chiral catalysts, etc. The effect of low cost, low production cost and easy preparation

Active Publication Date: 2018-10-16
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In traditional chemical synthesis methods, the introduction of chiral centers mainly contains three ways: (1) using chiral compounds as raw materials; (2) chemical resolution; (3) asymmetric synthesis of chiral catalysts; the three methods Both have the disadvantages of poor economy, chiral raw materials and chiral catalysts are expensive, and the chemical resolution method has low atom utilization
At the same time, chemical synthesis more or less uses toxic and harmful substances, such as thionyl chloride, pyridine, etc., the route is long, the comprehensive yield is low, and the amount of three wastes is large

Method used

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  • Preparation methods of immobilized nitrile group hydratase and (S)-N-ethylpyrrolidine-2-formamide
  • Preparation methods of immobilized nitrile group hydratase and (S)-N-ethylpyrrolidine-2-formamide
  • Preparation methods of immobilized nitrile group hydratase and (S)-N-ethylpyrrolidine-2-formamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Preparation of carboxylated carbon nanotubes:

[0053] In a dry and clean reactor, add 30g carbon nanotubes (purity 95%, Chengdu Organic Chemistry Co., Ltd., Chinese Academy of Sciences) and 60mL mixed acid (mass fraction 98% concentrated sulfuric acid: mass fraction 68% concentrated nitric acid volume ratio is 3:1, The volume dosage is 2mL / g based on the mass of carbon nanotubes) After ultrasonic treatment for 1 hour, heat and reflux for 12 hours to react, filter, wash with distilled water until the pH is 7.0, and dry under reduced pressure and vacuum at 50°C to obtain carboxylated carbon nanotubes. Tube.

Embodiment 2

[0055] Preparation of cyclodextrin-carbon nanotube-immobilized nitrile hydratase (abbreviated as E1):

[0056] (1) Feeding amount: carboxylated carbon nanotube 5g; N,N-dimethylformamide is an organic base, and the feeding amount is 0.25g, and its quality consumption is 5% g / g of the quality of carboxylated carbon nanotube; Chlorine Sulfoxide 25g, its quality dosage is 5 times g / g of carboxylated carbon nanotube quality; Cyclodextrin (98%, Shanghai Aladdin Biochemical Technology Co., Ltd., viscosity 200-400mPa.s) is polysaccharide, and feed amount 15g, its mass dosage is 3 times g / g of carboxylated carbon nanotube quality; Triethylamine is an organic amine, the feeding amount is 10g, its mass dosage is 2 times of carboxylated carbon nanotube quality g / g; N,N -Dimethylformamide is the organic solvent A, the feeding amount is 150mL, and its volume consumption is 30mL / g in terms of carboxylated carbon nanotube quality;

[0057] In a dry and clean reactor, add thionyl chloride, ca...

Embodiment 3

[0061] Preparation of chitosan-carbon nanotube-immobilized nitrile hydratase (abbreviated as E2):

[0062] (1) Feeding amount: carboxylated carbon nanotube 5g; N,N-dimethylacetamide is an organic base, and the feeding amount is 0.5g, and its quality consumption is 10% g / g of the quality of carboxylated carbon nanotube; Chlorine Sulfoxide 40g, its quality consumption is 8 times g / g of carboxylated carbon nanotube quality; The quality dosage is 5 times g / g of the quality of carboxylated carbon nanotubes; dimethylaminopyridine is an organic amine, and the feeding amount is 15g, and its quality dosage is 3 times g / g of the quality of carboxylated carbon nanotubes; DMSO is organic solvent A , the feeding amount is 150mL, and the volumetric dosage is 30mL / g based on the mass of carboxylated carbon nanotubes;

[0063] The reaction temperature was 100° C., the reaction time was 48 hours, and other operations were the same as in Example 2 to obtain a chitosan-carbon nanotube composite...

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Abstract

The invention discloses a preparation method of immobilized nitrile group hydratase and a method for catalytic preparation of (S)-N-ethylpyrrolidine-2-formamide through the immobilized nitrile group hydratase. Firstly, a carbon nanotube is adopted to be subjected to carboxylation and acylating chlorination and then reacts with polysaccharide to prepare a polysaccharide-modified carbon nanotube composite, and then through absorption, the immobilized nitrile group hydratase having high activity and capable of being recycled is prepared. A substrate, namely 2-cyano group-N-ethylpyrrolidine is subjected to amidation by taking the immobilized nitrile group hydratase as a catalyst, and the (S)-N-ethylpyrrolidine-2-formamide product with the high yield and high optical activity is obtained. The process is concise, the application range is wide, environmental pollution is small, the atom utilization rate is high, and the preparation methods are each an environment-friendly process.

Description

technical field [0001] The invention relates to the field of biomedicine, in particular to a preparation method of immobilized nitrile hydratase and (S)-N-ethylpyrrolidine-2-carboxamide. Background technique [0002] Sulpiride is a new type of antipsychotic drug first synthesized by Delagrange in France in 1967. Unlike traditional antipsychotic drugs, sulpiride only selectively blocks D2 receptors (dopamine receptors). Slight side effects of the vertebral system are its outstanding advantages. The drug has few side effects and a wide range of treatment. It has names such as "relationship regulating drug", "emotional activator" and "anti-loneliness agent". Levosulpiride is the L-body of sulpiride, which has the same purpose as sulpiride, but its dose is only half or less, and its toxic and side effects are also small. Levosulpiride can be obtained by resolution of sulpiride, but because of its low yield and difficult separation and purification, it is usually used in industr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12N11/10C12N11/14C12N9/88C12P17/10
CPCC12N9/88C12N11/10C12N11/14C12P17/10C12Y402/01084
Inventor 贾建洪冯东叶孙斌胡成坤张久明
Owner ZHEJIANG UNIV OF TECH
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