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Preparation of alanyl glutamine dipeptide compound

A technology of alanyl glutamine and peptide compounds, which is applied in the field of preparation of alanyl glutamine dipeptide compounds, can solve problems such as restrictions on popularization and application, high price, and difficulty in obtaining halogenated propionyl halides. The effect of simple process and cost reduction

Inactive Publication Date: 2005-10-12
上海依福瑞实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that optically pure halopropionyl halides are difficult to obtain and expensive
In addition, in each of the above preparation methods, only one of the two diastereomers of L-alanyl-L-glutamine and D-alanyl-L-glutamine can be obtained each time, so Its promotion and application are limited

Method used

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  • Preparation of alanyl glutamine dipeptide compound
  • Preparation of alanyl glutamine dipeptide compound
  • Preparation of alanyl glutamine dipeptide compound

Examples

Experimental program
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Effect test

Embodiment 1

[0007] 1. Preparation of N-(α-chloropropionyl)-L-glutamine

[0008] Add 16.0g (0.11 mol) of L-glutamine to 100ml of water and 50ml of toluene at room temperature and mix them. After cooling to 3°C±1°C, add 22ml (0.11mol) of 5N sodium hydroxide aqueous solution to make - Glutamine dissolved. Then, maintaining the above temperature, dropwise added 14.0 g of α-chloropropionyl chloride (0.11 mol), 30 ml of toluene and 25 ml of 5N sodium hydroxide aqueous solution into the above solution within 2 hours. Adjust the pH value to 9-11 with 5N sodium hydroxide, react at a temperature of 10°C for 2 hours, and separate the organic layer. 20 g of sodium chloride was added to the mixed solution after separating the organic layer at room temperature. Use concentrated hydrochloric acid to adjust the pH value to 2.5 and stir for 30 minutes, then use concentrated hydrochloric acid to adjust the pH value to 1.0, and keep it at room temperature for 4 hours. After filtering and drying the precip...

Embodiment 2

[0012] 1. Preparation of N-(α-chloropropionyl)-L-glutamine

[0013] Add 16.0g (0.11 mol) of L-glutamine to 50ml of water and 25ml of toluene at room temperature and mix. After cooling to 4°C±1°C, add 22ml (0.11mol) of 5N sodium hydroxide aqueous solution to make L - Glutamine dissolved. Then keep the above temperature, dropwise add 28.0g α-chloropropionyl chloride (0.22 mol), 60ml toluene and 50ml 5N sodium hydroxide aqueous solution to the above solution within 4 hours. Adjust the pH value to 9-11 with sodium hydroxide, react at a temperature of 15° C. for 2 hours, and separate the organic layer. 20 g of sodium chloride was added to the mixed solution after separating the organic layer at room temperature. Use concentrated hydrochloric acid to adjust the pH value to 2.5 and stir for 30 minutes, then use concentrated hydrochloric acid to adjust the pH value to 1.0, and keep it at room temperature for 4 hours. After filtering and drying the precipitated crystals, 20.0 g of N-...

Embodiment 3

[0017] 1. Preparation of N-(α-bromopropionyl)-L-glutamine

[0018] Add 16.0g (0.11 mol) of L-glutamine to 100ml of water and 50ml of toluene at room temperature and mix them. After cooling to 3°C±1°C, add 22ml (0.11mol) of 5N sodium hydroxide aqueous solution to make - Glutamine dissolved. Then keep the above temperature, dropwise add aqueous solution containing 17.8g α-bromopropionyl chloride (0.11 mol), 30ml toluene and 25ml sodium hydroxide to the above solution within 2 hours. Adjust the pH value to 9-11 with sodium hydroxide, react at 10°C for 2 hours, and separate the organic layer. 20 g of sodium chloride was added to the mixed solution after separating the organic layer at room temperature. Use concentrated hydrochloric acid to adjust the pH value to 2.5 and stir for 30 minutes, then use concentrated hydrochloric acid to adjust the pH value to 1.0, and keep it at room temperature for 4 hours. After filtering and drying the precipitated crystals, 25.8 g of N-(α-bromop...

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Abstract

Production of alanyl glutamine dipeptide compound is carried out by adding L-glutamine into mixed liquid of methylbenzene and water, cooling, adding into sodium hydrate, dissolving L-glutamine, dripping into solution with alpha - halopropacyl halide, methylbenzene and sodium hydrate, regulating pH, reacting, separating organic layer, adding sodium chloride into solution with organic layer separation, regulating pH, adding into concentrated chlorhydric acid, regulating pH, laying aside, filtering, separating out crystal, drying crystal, reacting with ammonia water, controlling temperature and pressure, cooling, de-pressuring, concentrating, adding water, dripping into methyl alcohol, laying aside, filtering, separating out L-alanyl-L-glutamate crude products, purifying and obtaining refined products. It achieves simple process and low cost.

Description

Technical field: [0001] The invention relates to a preparation method of alanyl glutamine dipeptide compound, especially a preparation method of L-alanyl-L-glutamine dipeptide compound. Background technique: [0002] The preparation method of existing alanylglutamine dipeptide compound, such as European patent (EPNO311.057) generates activation with benzyloxycarboalanine (Z-ALa) in the presence of dicyclohexylcarbodiimide (DCC) Lipid, then condensed with glutamine (Gln) to form a dipeptide, and then deprotected by catalytic hydrogenation. This method has long steps and requires hydrogenation to deprotect the group. Another example is the Journal of Physiological Chemistry, 1919, page 58, volume 105, using 2-bromopropionyl chloride to acylate glutamine (Gln) to generate intermediate 2-bromopropionyl glutamine, which is then ammoniated to obtain dipeptide L-Alanyl-L-Glutamine. This method is difficult to use in production due to low yield and low optics. In European Patent...

Claims

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Application Information

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IPC IPC(8): C07K5/06
Inventor 许云生葛邦錀曾德祥
Owner 上海依福瑞实业有限公司
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