Synthesis method of dipeptide containing L-glutamine

A technology of glutamine dipeptide and synthesis method, which is applied in the field of synthesis of L-glutamine dipeptide, can solve the problem of low yield of the target product, and achieve the effects of increasing yield, reducing cost, and low production cost

Inactive Publication Date: 2007-02-07
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method does not require protecting groups, it is easy to produce by-products such as tripeptides, resulting in low yield of the target product

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The preparation of embodiment 1 L-alanyl-L-glutamine, its specific steps are:

[0024] (1) Preparation of phthalyl-L-alanine: 44.5 grams of L-alanine and 74 grams of phthalic anhydride are mixed into a round-bottomed flask, heated to 135-140°C in an oil bath, and React at high temperature for 30 minutes while hot and pour it into hot water, cool to crystallize, and recrystallize the obtained crystals with 30% ethanol to obtain 102 grams of phthaloyl-L-alanine with a yield of 93%.

[0025] (2) Preparation of phthalyl-L-alanyl-L-glutamine: 43.8 grams of phthalyl-L-alanine and 20.4 grams of triethylamine were dissolved in 350 milliliters of ethyl acetate, The solution was cooled to -5°C, then 21.6 grams of ethyl chloroformate was added, and after 25 minutes, 250 milliliters of precooled sodium bicarbonate solution containing 29.2 grams of L-glutamine was added, and the ice-salt bath was removed after stirring for 2 hours. Leave at room temperature for 12 hours. The aqueo...

Embodiment 2

[0027] The preparation of embodiment 2 L-alanyl-L-glutamine, its specific steps are:

[0028] (1) Preparation of phthalyl-L-alanine: dissolve 72.5 grams of phthalimide and 70 milliliters of dimethylethylamine in 350 milliliters of N,N-dimethylformamide, The solution was cooled to 5-10°C, and 50 ml of ethyl chloroformate was added dropwise. After adding the sample, it was stirred and reacted for 2 hours. The reaction solution was poured into 2 liters of water to precipitate 97 g of N-ethyl formate phthalimide. The rate is 88%. Dissolve 17.8 grams of L-alanine and 21.2 grams of sodium carbonate in 200 milliliters of water, add 45 grams of N-ethyl formate phthalimide, stir at room temperature for 2 hours, filter the reaction solution, and acidify the filtrate with 6N hydrochloric acid to obtain Phthaloyl-L-alanine was recrystallized with 30% ethanol to obtain 42 g of the product, with a yield of 96%.

[0029] (2) Preparation of phthaloyl-L-alanyl-L-glutamine: the specific opera...

Embodiment 3

[0031] The preparation of embodiment 3 glycyl-L-glutamine, its specific steps are:

[0032] (1) Preparation of phthaloylglycine: the specific operation steps are the same as in Example 1, and the yield is 96%.

[0033](2) Phthalylglycyl-L-glutamine preparation: 41 grams of phthalylglycine and 20.4 grams of triethylamine are dissolved in 350 milliliters of N, N-dimethylformamide, and the solution is cooled to -5°C, then add 24.6 g of isopropyl chloroformate, add 250 ml of pre-cooled sodium bicarbonate solution containing 29.2 g of L-glutamine after 25 minutes, stir and react for 2 hours, remove the ice-salt bath, and Leave for 12 hours. The solvent was distilled off under reduced pressure, the solid was dissolved in water, and the insoluble matter was removed by filtration. The filtrate was acidified with 6N hydrochloric acid to precipitate phthaloylglycyl-L-glutamine, which was recrystallized with 30% ethanol to obtain 38.6 g of the product. Yield 58%.

[0034] (3) Preparat...

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Abstract

A process for preparing L-glutamine dipeptide includes such steps as preparing phthaloyl amino acid by use of phthaloyl as the protector of amino acid, condensating reaction on L-glutamine to obtain phthaloyl-L-glutamin dipeptide, and using hydrazine hydrate to remove phthaloyl.

Description

1. Technical field [0001] The invention relates to a synthesis method of L-glutamine dipeptide, belonging to the field of chemical synthesis. 2. Technical background [0002] L-glutamine is a conditionally essential amino acid, which plays an important role in the body's immune function and wound repair. Recent studies have shown that L-glutamine plays an important role in body metabolism [Abumrad, N.N. et al, Am. J. Physiol. 1989, 257, E228]. Due to the low thermal stability and low water solubility of L-glutamine, its use is limited. In addition, L-glutamine is easily decomposed into pyrrolidone acid and ammonia in aqueous solution, which is harmful to the body. The small peptide containing L-glutamine makes up for the deficiency of L-glutamine, and it has high thermal stability and water solubility. [0003] Now known methods for preparing alanyl-glutamine (Lipeptide) have the following three kinds: [0004] (1) react intermediate product D-2-halogen-propionyl-L-glutam...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/06
Inventor 焦庆才钱绍松陈然吴晓燕刘毅
Owner NANJING UNIV
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