Preparation of N(2)-L-alanyl-L-glutamine

A technology of glutamine and alanyl, which is applied in the field of preparation of N-L-alanyl-L-glutamine, can solve the problems of high amino acid price and high process cost, and achieves simple process, low cost and low toxicity. Effect

Inactive Publication Date: 2009-06-24
TIANJIN TIANCHENG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The N-terminally protected amino acid used in this method has a higher price, resulting in a higher cost of the whole process

Method used

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Examples

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Embodiment

[0022] 1. Preparation of N(2)-D-α-chloropropionyl-L-glutamine

[0023] Pour 31ml of water and 31ml of toluene into the reaction flask and mix evenly, start stirring, add 10g of L-glutamine, and cool to 5°C. Slowly add 5N sodium hydroxide dropwise to make the pH value of the solution reach 10, and the L-glutamine is completely dissolved. At the same time, 10.6ml of anhydrous toluene containing 8.5g D-α-chloropropionyl chloride and 5N sodium hydroxide were added dropwise to the above solution within 2 hours, and the pH value was adjusted with sodium hydroxide to keep the pH value of the solution at 10. A total of 29.5ml of sodium hydroxide was added twice, and the temperature was kept at 5°C; after the dropwise addition, the stirring was continued for 1 hour while maintaining the temperature at 5°C. Stop stirring then, carry out cooling; Static layering, separate the toluene layer, under room temperature, 12.6g sodium chloride is added in the mixed solution that does not have t...

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PUM

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Abstract

The invention discloses a method for preparing N(2)-L-alanyl-L-glutamine, belonging to a method for preparing dipeptide containing four amino acids at most. The method comprises the following steps: (1) inorganic base is added into the solution of toluene and water which contains L-glutamine; then the mixture of D-alpha-chloropropionyl chloride and toluene is added and the pH value of reaction solution is controlled between 9.5 and 10.5 by the inorganic base; the reaction temperature is maintained between 0-5 DEG C; the reaction solution is quiescent so that a toluene layer is separated; sodium chloride is added into the remaining solution at room temperature and N(2)-D-alpha-chloropropionyl-L-glutamine is obtained after filtration and drying; ammonia is added into the N (2)-D-alpha-chloropropionyl-L-glutamine, and concentrated solution after concentration under reduced pressure is transferred to a crystallizer; methanol is added and a crude product is obtained after filtration and drying; a refined product of the N (2)-L-alanyl-L-glutamine is obtained by refining.

Description

technical field [0001] The present invention relates to a method for preparing dipeptides containing up to 4 amino acids, especially N(2)-L-alanyl-L-glutamine. Background technique [0002] Amide amino acids are an extremely useful class of amino acids. For example, glutamine has many important physiological functions: it can promote the proliferation of gastrointestinal mucosal cells and maintain the integrity of the intestinal tract; the phagocytosis of macrophages, the proliferation of lymphocytes and the synthesis of proteins must rely on sufficient glutamine . Under normal circumstances, the human body can synthesize glutamine to meet its own needs. However, under stress conditions such as major trauma and severe infection, the body is in an ultra-high metabolic state, and the body's glutamine pool is severely consumed. At the same time, other tissues and organs such as the small intestine and lymphocytes increase the intake of glutamine in the blood. , so that plasm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/06
Inventor 张国基
Owner TIANJIN TIANCHENG PHARMA
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