Prepn process of L-alanyl-L-glutamine

A technology of halogenated propionyl glutamine and glutamine, which is applied in the field of preparation of L-alanyl-L-glutamine, can solve the production cost of human hazards, L-alanyl-L-glutamine Problems such as the complex preparation process of amide, to achieve the effect of being beneficial to environmental protection, good industrial application value, and less by-products

Inactive Publication Date: 2007-03-21
湖北浩信药业有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The object of the present invention is to provide a simple process, low cost and high yield in order to overcome the disadvantages of complex preparation process o

Method used

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  • Prepn process of L-alanyl-L-glutamine

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Embodiment 1

[0021]D-2-chloropropionic acid (35.8 g, 0.33 mol) was dissolved in 200 mL of benzene at room temperature, and the condensing agent 2-chloro-1,3-dimethylimidazoline hydrochloride (61.2 g, 0.36 mol), added glutamine (46.9 g, 0.33 mol) after 4 hours of reaction, filtered after 2 hours of reaction, washed with 5 wt% hydrochloric acid and water to obtain D-2-halopropionylglutamine. The obtained product was directly added to 28 wt% ammonia water (800 ml), reacted at 75° C. for 6 hours under a pressure of 2 kg / cm 2 , cooled, concentrated under reduced pressure, added with ethanol, and left to separate out crystals to obtain 47.6 g of L- Alanyl-L-glutamine product, yield 66.5%; optical purity 98.5%.

[0022] The above product was recrystallized from methanol-water (volume ratio 2:1) to obtain L-alanyl-L-glutamine product with an optical purity of 99.8%, melting point: 216°C (decomposition); specific optical rotation: [α] 20 =-3.49 (C=10, 1 mol / L HCl).

Embodiment 2

[0024] At room temperature, D-2-bromopropionic acid (61.2 g, 0.4 mol) was dissolved in 300 mL of toluene, 2-chloro-1,3-dimethylimidazoline hydrochloride (68.0 g, 0.4 mol) was added ), after 4 hours of reaction, glutamine (49.7 g, 0.35 mol) was added, filtered after 2 hours of reaction, washed with 5wt% hydrochloric acid and water to obtain D-2-bromopropionylglutamine. The obtained product was directly added to 28% by weight ammonia water (1000 ml), reacted at 45° C. for 6 hours at 2 kg / cm 2 , cooled, concentrated under reduced pressure, added with ethanol, and left to separate out crystals to obtain 55.9 g of L-propane. Aminoacyl-L-glutamine product, yield 73.6%, optical purity 98.8%.

[0025] The above product was recrystallized from ethanol-water (volume ratio 5:1) to obtain L-alanyl-L-glutamine product with an optical purity of 99.9%, melting point: 216°C (decomposition); specific optical rotation: [α] 20 =-3.45 (C=10, 1 mol / L HCl).

Embodiment 3

[0027] D-2-chloropropionic acid (32.6 g, 0.30 mol) was dissolved in 250 mL of toluene at room temperature, 2-chloro-1,3-dimethylimidazoline hydrochloride (42.5 g, 0.25 mol) was added ), added glutamine (42.6 g, 0.30 mol) after 5 hours of reaction, filtered after 2 hours of reaction, washed with 5 wt% nitric acid and water to obtain D-2-halopropionyl glutamine. The obtained product was directly added to 28% by weight ammonia water (900 ml), reacted at 60° C. for 6 hours under a pressure of 3 kg / cm 2 , cooled, concentrated under reduced pressure, added with methanol, and left to separate out crystals to obtain 42.9 g of L- Alanyl-L-glutamine product, yield 65.9%; optical purity 97.8%.

[0028] The above product was recrystallized from tetrahydrofuran-water (volume ratio 1:2) to obtain L-alanyl-L-glutamine product with an optical purity of 99.8%, melting point: 216°C (decomposition); specific optical rotation: [α] 20 =-3.40 (C=10, 1 mol / L HCl).

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Abstract

The preparation process of L-alanyl-L-glutamine includes the first condensation reaction between D-2-halopropionic acid and glutamine inside inert solvent and in the presence of condensing agent and acidification to obtain D-2-halopropionyl glutamine; and the aminolysis reaction of the obtained D-2-halopropionyl glutamine with ammonia water to obtain L-alanyl-L-glutamine. The preparation process of the present invention is simple, and has the advantages of less reaction steps, less pollution, facile material, easy separation of the final product, low production cost, short production period and high product yield.

Description

technical field [0001] The present invention relates to a preparation method of L-alanyl-L-glutamine. Background technique [0002] Amino acids are a class of extremely useful amino acids. For example, glutamine (Gln) is the most abundant amino acid in the body and has many extremely important physiological functions, such as promoting the proliferation of gastrointestinal mucosal cells and maintaining the integrity of the intestinal tract. Moreover, the phagocytosis of macrophages, the proliferation of lymphocytes and the synthesis of proteins must all depend on sufficient glutamine. Most tissues in the body can synthesize glutamine. Under normal conditions, it can fully meet the needs of the body. However, under various stress conditions such as trauma and infection, the body is in a state of ultra-high metabolism, and skeletal muscle proteins are decomposed in large quantities. Glutamine is released from the blood, and the body's glutamine pool is severely depleted. At ...

Claims

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Application Information

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IPC IPC(8): C07K5/06
Inventor 姜能桥刘文杰
Owner 湖北浩信药业有限公司
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