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Technical preparation method of glycyl glutamine

A technology of glycylglutamine and glutamine, applied in the direction of peptides, etc., can solve the problems of difficult removal of triethylamine, influence of drip acceleration rate, and high equipment requirements, so as to achieve easy control of the reaction, reduce equipment cost, and improve the reaction The effect of efficiency

Inactive Publication Date: 2015-05-27
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The double-dropping in this method has higher requirements on reaction control, and the pH value of the reaction system is easily affected by the drop rate of acid chloride and sodium hydroxide, which is easy to cause the pH value to be too low and cause the reaction to be difficult to proceed forward, which seriously affects the product. rate, and even cause the reaction to fail
And this method is also higher to equipment requirement, does not utilize to reduce production cost and realize industrialization
In addition, the triethylamine added in the hydrazinolysis process of this method is difficult to remove in the subsequent purification steps, resulting in a decrease in product yield and purity

Method used

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  • Technical preparation method of glycyl glutamine

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Effect test

Embodiment 1

[0021] (1) Add 8.52g of sodium carbonate, 11.74g of glutamine, 100mL of water and 40mL of toluene into a four-neck flask, place it in a low-temperature tank, stir and cool down to -2°C. Slowly add 16.4 g of freshly prepared phthaloylglycyl chloride (prepared from phthaloylglycine and thionyl chloride in 40 mL of toluene) to the above low-temperature stirred glutamine solution, dropwise The addition process lasted 4 hours and 20 minutes. When the dropwise amount of acid chloride reached 90%, it was found that the pH value of the reaction solution was 8, and then 2.0 g of sodium bicarbonate solid was added. After the acid chloride has been added dropwise, withdraw from the low-temperature tank, stir and naturally heat up. Then the lower aqueous phase was extracted, and concentrated hydrochloric acid was added dropwise until the pH was about 2.5, and a large amount of white solid precipitated. Finally, it was dried by suction filtration under low pressure to obtain 22.9 g of ph...

Embodiment 2

[0024] (1) Add 82.9g of potassium carbonate, 88.1g of glutamine, 750mL of water and 300mL of toluene into a four-necked flask, place it in a low-temperature tank, stir and cool down to -1°C. 123.0 g of freshly prepared phthaloylglycyl chloride (prepared from phthaloylglycine and thionyl chloride in 300 mL of toluene) was slowly added dropwise to the above low-temperature stirring glutamine solution, and the whole dropwise The addition process lasted 5 hours. When the dropwise amount of acid chloride reaches 92%, it is found that the pH value of the reaction solution is 8, then 9.0g potassium bicarbonate solid is added, and when the dropwise amount of acid chloride reaches about 97%, it is found that the pH value of the reaction solution is 8 , and then add 8.0 g of potassium bicarbonate solid. After the acid chloride has been added dropwise, withdraw from the low-temperature tank, stir and naturally heat up. Then the lower aqueous phase was extracted, and concentrated hydroc...

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Abstract

The invention discloses a technical preparation method of glycyl glutamine. The technical preparation method comprises the following steps: firstly, mixing glutamine with carbonate water solution, wherein the generated bicarbonate can provide a continuous and stable weak alkali environment for the low-temperature dropwise addition process of phthalimide acetyl chloride, further the side product hydrochloric acid generated during low-temperature condensation reaction of glutamine and phthalimide acetyl chloride can be immediately eliminated, the reaction efficiency is greatly improved, the reaction process is easily controlled, the procedure of synchronously controlling the dropwisde addition of strong base alkali solution during the traditional synthesis according to the reaction rate can be reduced, and the side reaction between strong base and phthalimide acetyl chloride can also be limited; then hydrazinolyzing the obtained phthalimide acetyl-glutamine with excessive hydrazine hydrate, to obtain glycyl glutamine, so that the use of triethylamine difficult to separate can be avoided. According to the technical preparation method, the technology is simple and easy to control, the operability is strong, both the reaction efficiency and content are high, equipment cost is low and the industrialization is easy.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and relates to a process preparation method of glycyl glutamine. Background technique [0002] Glutamine (GLN) is a carrier for transporting nitrogen in organisms. It plays an important role in protein and DNA synthesis, intestinal cell growth and metabolism, immune system, etc. It is an indispensable free amino acid for the human body. Glycyl-L-glutamine, as an active dipeptide that supplements exogenous glutamine to the human body, is widely used in intestinal barrier function protection, surgical trauma recovery, cardiomyocyte therapy after burns, immune function regulation, etc. It effectively solves the problem that the development of glutamine is limited due to its instability and low solubility, and further promotes its development and application as a nutritional preparation. [0003] At present, various preparation methods of glycyl-L-glutamine have been disclosed...

Claims

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Application Information

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IPC IPC(8): C07K5/062
Inventor 马科锋任玉潘雄飞吴佳婷孙爱武
Owner NANJING UNIV OF SCI & TECH
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