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Method for preparing optical pure selenium - methyl selenium substituted aminothiopropionic acid by employing enzymatic resolution of racemic selenium- methyl selenium substituted aminothiopropionic a

A technology for the separation of methylselenocysteine ​​and enzymatic method, which is applied in the direction of fermentation, etc., and can solve the problems of no reports on the separation of seleno-methylselenocysteine

Active Publication Date: 2008-04-09
江西川奇药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there is no report on the resolution of seleno-methylselenocysteine

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] (1) Preparation of N-acetyl-selenium-methylselenocysteine:

[0016] Get 18.2 grams of vortex selenium-methylselenocysteine ​​and place it in a 250 ml three-neck flask with a condensing reflux tube, a thermometer and a stirrer, dissolve 10 grams of NaOH in 100 ml of water, add it to the flask after cooling , stirred to completely dissolve the selenium-methylselenocysteine, then slowly add 14 ml of acetic anhydride dropwise, and control the reaction temperature at 0°C. Stir for about 30 hours after the addition, and detect no amino acid reaction with ninhydrin. Use hydrochloric acid to adjust the pH to 1-2, then extract with ethyl acetate, combine the organic phases and evaporate the solvent to dryness under reduced pressure to obtain a solid, which is dissolved in methanol, and the insoluble matter is removed by filtration. Crystallized to obtain 20.44 g of vortex N-acetyl-selenium-methylselenocysteine, with a yield of 91.25%.

[0017] (2) Resolution of vortex N-acetyl...

Embodiment 2

[0022] (1) Preparation of N-acetyl-selenium-methylselenocysteine:

[0023] Get 18.2 grams of vortex selenium-methylselenocysteine ​​and place it in a 250 ml three-neck flask with a condensing reflux tube, a thermometer and a stirrer, dissolve 10 grams of NaOH in 100 ml of water, add it to the flask after cooling , stirred to completely dissolve the selenium-methylselenocysteine, then slowly add 14 ml of acetic anhydride dropwise, and control the reaction temperature at 30°C. Stir for about 24 hours after the addition, and detect no amino acid reaction with ninhydrin. Use hydrochloric acid to adjust the pH to 1-2, then extract with ethyl acetate, combine the organic phases and evaporate the solvent to dryness under reduced pressure to obtain a solid, which is dissolved in methanol, and the insoluble matter is removed by filtration. Crystallization yielded 21.35 g of vortex N-acetyl-selenium-methylselenocysteine, with a yield of 95.31%.

[0024] (2) Resolution of vortex N-acet...

Embodiment 3

[0029] (1) Preparation of N-acetyl-selenium-methylselenocysteine:

[0030] Get 18.2 grams of vortex selenium-methylselenocysteine ​​and place it in a 250 ml three-neck flask with a condensing reflux tube, a thermometer and a stirrer, dissolve 10 grams of NaOH in 100 ml of water, add it to the flask after cooling , stirred to completely dissolve selenium-methylselenocysteine, and then slowly add 14 ml of acetic anhydride dropwise, and control the reaction temperature at 60°C. Stir for about 20 hours after the addition, and detect no amino acid reaction with ninhydrin. Use hydrochloric acid to adjust the pH to 1-2, then extract with ethyl acetate, combine the organic phases and evaporate the solvent to dryness under reduced pressure to obtain a solid, which is dissolved in methanol, and the insoluble matter is removed by filtration. Crystallization yielded 21.20 g of vortex N-acetyl-selenium-methylselenocysteine, with a yield of 94.64%.

[0031] (2) Resolution of vortex N-acet...

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Abstract

The invention discloses a method utilizing enzyme measure to separate a mixed rotating selenium-methyl selenocysteine to prepare an optical pure selenium-methyl selenocysteine. The method acerylates the mixed rotating selenium-methyl selenocysteine with erhyl anhydride in sodium hydroxide solution and acidificates with hydrochloride to achieve a mix N ethyl acyl selenium methyl selenocysteine. Then, in certain PH value, reaction temperature, enzyme amount, substrate and cobalt ion concentration, the mix N ethyl acyl selenium methyl selenocysteine is separated by acylate enzyme I of swine renal to obtain an oprical pure L selenium methyl selenocysteine and an N ethyl D selenium methyl selenocysteine. And finally the N ethyl D selenium methyl selenocysteine is heated and hydrolyzed with hydrochloride and is neutralized with ammonia water to obtain an optical pure D selenium methyl selenocysteine. The method has the advantages of convenient for operating and low in cost, which is suitable for industrialized production of the optical pire selenium methyl slenocysteine.

Description

technical field [0001] The invention relates to a method for preparing optically pure selenium-methylselenocysteine ​​by decomposing helical selenium-methylselenocysteine ​​by enzymatic method. Background technique [0002] L-type selenium-methylselenocysteine ​​is a natural selenium-containing amino acid that widely exists in plants such as garlic, onion, and broccoli, as well as selenium-enriched yeast. It is the 21st amino acid-selenocysteine derivative. It has the functions of anti-cancer, anti-oxidation, anti-aging, improving immunity, treating cardiovascular and cerebrovascular diseases, detoxifying heavy metals, preventing and treating Keshan disease, Kaschin-Beck disease, etc. It can be used as an efficient and safe selenium trace element supplement agent. D-type selenium-methylselenocysteine ​​is an unnatural amino acid, which is an optical isomer of L-type selenium-methylselenocysteine. The physical and chemical properties of the two are almost the same under nor...

Claims

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Application Information

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IPC IPC(8): C12P41/00
Inventor 刘建群张小平尹家琪刘小辉
Owner 江西川奇药业有限公司
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