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Green and efficient method for preparing L-selenium methylselenocysteine

A technology of selenocysteine ​​and selenomethyl, applied in the field of green and efficient preparation of L-selenomethyl selenocysteine, which can solve the problems of harsh reaction conditions, environmental pollution, and high equipment requirements, and meet the requirements of the reaction conditions Moderate, avoid environmental pollution, overcome the effect of instability

Active Publication Date: 2019-12-31
河南希百康健康产业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] (2) Sodium methylselenide method: use methylselenolate to replace chlorine in 3-chloroalanine and its derivatives to obtain selenomethylselenocysteine. This method depends on the source of raw materials for chloroalanine Difficult, high production cost, low yield, not conducive to large-scale production
[0022] In summary, these synthetic methods have their own shortcomings, such as: difficult source of raw materials, high price; complex synthesis process, low yield; harsh reaction conditions, high equipment requirements; involving strong acid and highly toxic raw materials, serious environmental pollution; and target The molecule is a racemate (DL-configuration), needs to be resolved, etc., so they are difficult to achieve large-scale production

Method used

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  • Green and efficient method for preparing L-selenium methylselenocysteine
  • Green and efficient method for preparing L-selenium methylselenocysteine
  • Green and efficient method for preparing L-selenium methylselenocysteine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] A green and efficient method for preparing L-selenomethylselenocysteine, comprising the following steps:

[0058] (a) Add 50 g of L-serine methyl ester hydrochloride to 300 mL of tetrahydrofuran under stirring condition, and cool to 0~5°C;

[0059] (b) Add 70.8 g of triethylamine, stir well, then add 26.5 g of acetyl chloride dropwise (about 1 h to complete the dropwise addition), and continue to stir for 3 h after the dropwise addition; then slowly add 34.4 g of thionyl chloride dropwise ( 0.5 h), continue to stir for 1 h after the dropwise addition, raise the temperature to 45°C, stir for 3 h, then cool down to 0°C;

[0060] (c) Add 600 mL of saturated sodium bicarbonate solution, stir for 0.5 h, then add dropwise 300 mL of sodium methylselenide in tetrahydrofuran (containing 37.3 g of sodium methylselenide), dropwise for about 2 hours, continue stirring for 3 hours , warmed up to room temperature, and stirred for 12 h to obtain a reaction mixture;

[0061] (d) Afte...

Embodiment 2

[0082] A green and efficient method for preparing L-selenomethylselenocysteine, comprising the following steps:

[0083] (a) Add 50 g of L-serine methyl ester hydrochloride to 300 mL of tetrahydrofuran under stirring condition, and cool to 0~5°C;

[0084] (b) Add 70.8 g of triethylamine, stir evenly, then add 26.5 g of acetyl chloride dropwise (about 1 h to complete the dropwise addition), and continue to stir for 4 h after the dropwise addition; then slowly add 36.1 g of thionyl chloride dropwise ( 0.5 h), continue to stir for 1 h after the dropwise addition, raise the temperature to 45°C, stir for 3 h, then cool down to 0°C;

[0085] (c) Add 600 mL of saturated sodium bicarbonate solution, stir for 0.5 h, then add dropwise 300 mL of sodium methylselenide in tetrahydrofuran (containing 37.3 g of sodium methylselenide), dropwise for about 2 hours, continue stirring for 3 hours , warmed up to room temperature, and stirred for 12 h to obtain a reaction mixture;

[0086] (d) Af...

Embodiment 3

[0097] A green and efficient method for preparing L-selenomethylselenocysteine, comprising the following steps:

[0098] (a) Add 50 g of L-serine methyl ester hydrochloride to 300 mL of tetrahydrofuran under stirring condition, and cool to 0~5°C;

[0099] (b) Add 70.8 g of triethylamine, stir evenly, then add 27.8 g of acetyl chloride dropwise (about 1 h to complete the dropwise addition), and continue to stir for 4 h after the dropwise addition; then slowly add 37.8 g of thionyl chloride dropwise ( 0.5 h), continue to stir for 1 h after the dropwise addition, raise the temperature to 45°C, stir for 3 h, then cool down to 0°C;

[0100] (c) Add 600 mL of saturated sodium bicarbonate solution, stir for 0.5 h, then add dropwise 300 mL of sodium methylselenide in tetrahydrofuran (containing 37.3 g of sodium methylselenide), dropwise for about 2 hours, continue stirring for 3 hours , warmed up to room temperature, and stirred for 12 h to obtain a reaction mixture;

[0101] (d) Af...

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Abstract

The present invention discloses a green and efficient method for preparing L-selenium methylselenocysteine. Firstly, L-serine methyl ester hydrochloride is used as a starting raw material and an acetylation, chlorination and methylselenization one-pot method is used to synthesize a reaction substrate, and then the obtained reaction substrate is hydrolyzed under an action of enzyme catalysis to generate L-selenomethylselenocysteine. The one-pot method is used to prepare the reaction substrate, overcomes instability of intermediates and also reduces tedious steps of separation and purification of the intermediates; the enzyme catalysis hydrolysis is used to avoid environmental pollution and equipment corrosion caused by strong acid hydrolysis and overcome disadvantages of selenium-ether bondrupture, product racemization, etc. Characteristics are as follows: the raw materials are easy to obtain and cheap in price, the method is convenient to operate, reaction conditions are mild, green and environmentally protectively, and the product is simple, easy for separation, high in yield and suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of food additives, and in particular relates to a green and efficient method for preparing L-selenomethylselenocysteine. Background technique [0002] Selenium is an essential trace element for the human body and an important part of various enzymes in the human body. It has various functions such as anti-oxidation, anti-cancer, detoxification, promotion of growth, and improvement of immunity. Once the body is deficient in selenium, it will directly lead to cardiovascular and cerebrovascular diseases , high blood pressure, metabolic syndrome, gastrointestinal diseases, diabetes, asthma, Parkinson's disease, liver disease, cancer and other diseases. Therefore, selenium plays a huge role in human health that cannot be replaced by other substances. [0003] Most areas in the world are deficient in selenium, and 72% of the regions in my country are selenium-deficient areas, which need to be supplemented with sel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P13/12C07C391/00
CPCC12P13/12C07C391/00Y02P20/584
Inventor 王小松卢会芹王兴东王阳李霁宇
Owner 河南希百康健康产业有限公司
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