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Synthesis method of N-(2)-L-alanyl-L-glutamine

A glutamine and synthetic method technology, applied in the direction of peptides, etc., can solve the problems of difficult removal of by-products, low yield, high cost, etc., and achieve the effect of simple process, high operability, and low cost

Inactive Publication Date: 2013-05-08
QINGDAO VLAND BIOTECH INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method has few steps and is simple, but the cyclized product N-carboxylic acid anhydride in the middle of the reaction is unstable and easy to decompose, and the by-products are difficult to remove, and the final product is difficult to purify, so the yield is low. In addition, phosgene is a highly toxic substance, which is harmful to the environment and environment. Harmful to the human body
Utilize N-terminal protected amino acid to react with triphenylphosphine to generate active ester, then react with glutamine, then acidify with inorganic acid, remove the protecting group to obtain the product, this method is costly

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0019] 1. Synthesis of N(2)-D-α-chloropropionyl-L-glutamine

[0020] First add 300kg of water and 150kg of toluene to the reaction kettle, add 48.2kg of L-glutamine at room temperature, and ice-bath to 0-5°C. Add 66kg of 5N NaOH solution under stirring until L-glutamine is completely dissolved. Then slowly add 42Kg of D-2-chloropropionyl chloride in 90kg of toluene solution, and dropwise add 74kg of 5N NaOH solution at the same time to maintain the pH of the reaction solution at 10 (dropping for two hours). After the dropwise addition, the ice bath was continued at 0-5°C for 1 hour. Toluene was removed in layers. 60 kg NaCl was added to the aqueous phase at room temperature. Add 22kg of concentrated HCl, adjust the pH to 2.5, add seed crystals, and stir for half an hour. Add 8kg of concentrated hydrochloric acid to adjust the pH to 1, and let it stand still for 1 hour. Filter and dry to obtain the product. Melting point (decomposition temperature) 148°C, yield: 85.3%.

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Abstract

Belonging to preparation of immune dipeptide compounds, the invention discloses a synthesis method of N(2)-L-alanyl-L-glutamine. The preparation steps include: taking D-2-chloropropanoyl chloride and L-glutamine as raw materials, conducting condensation to obtain N-(D-2-propionyl chloride)-L-glutamine, then performing ammoniation to obtain N(2)-L-alanyl-L-glutamine, and carrying out refining so as to obtain a refined product.

Description

technical field [0001] The invention relates to a synthesis method of alanyl glutamine dipeptide compound, especially a synthesis method of N(2)-L-alanyl-L-glutamine. Background technique [0002] Amide amino acid is a kind of amino acid that is very abundant in the body. It is a participant in the metabolism of various tissues in the body and 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 Function, proliferation of lymphocytes and protein synthesis must depend on sufficient glutamine. Lack of glutamine can cause many diseases. Under various stress conditions, animals have a greatly increased demand for L-glutamine. Therefore, it is extremely necessary to supplement the body with L-glutamine. [0003] However, glutamine has low solubility and instability, and it will produce toxic pyroglutamic acid and ammonia after heating, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/062
Inventor 姚德勇郝智慧王艳玲
Owner QINGDAO VLAND BIOTECH INC
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