Process for preparing thymopentin

A pentapeptide and thymus technology, which is applied in the field of preparation of Jing-Lai-Tian-Val-Tyropentapeptide, can solve the problems of limited product quantity, waste, high risk and the like, and achieves low synthesis cost, prevention of side reactions, and high price. cheap effect

Inactive Publication Date: 2005-12-07
康哲(湖南)制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods are costly, and the feeding ratio is generally 3 to 5 times, resulting in a lot of waste
The solid-phase synthesis method also requires a peptide solid-phase synthesizer, which is costly
In addition, amino acids with side chain protection are expensive, such as tyrosine with side chain protection needs to go through a violent HF deprotection reaction at the end of synthesis
Due to the high toxicity of HF, the risk of reaction is relatively high, and a special HF deprotection device must be equipped.
And because the volume of the reaction vessel of this type of deprotection device is limited, the number of products obtained from each deprotection is limited, thus limiting the application in industry

Method used

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  • Process for preparing thymopentin
  • Process for preparing thymopentin
  • Process for preparing thymopentin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0060] The present invention will be further illustrated by non-limiting examples below.

[0061] Herein, the abbreviations for the reagents used are:

[0062] DCC: Dicyclohexylcarbodiimide

[0063] HOBt: 1-Hydroxybenzotriazole

[0064] NMM: N-methylmorpholine

[0065] THF: Tetrahydrofuran

Embodiment

[0067] 1. Preparation of Boc-Val-Tyr-OMe

[0068] 3.52g (15.2mmol) of HCl·Tyr-OMe was dissolved in 20ml of anhydrous tetrahydrofuran, the resulting solution was adjusted to pH 7-8 with N-methylmorpholine, cooled to 0°C for later use.

[0069] 3.29g (15.2mmol) Boc-L-Val-OH, 2.15g (16.0mmol) HOBt were dissolved in anhydrous tetrahydrofuran, cooled to 0°C, slowly added 3.29g (16.0mmol) DCC, stirred at 0°C for 5 minutes. Then mix with the above solution, stir at 0°C for 2 hours, maintain pH 8-9 with N-methylmorpholine, stir at room temperature for 10 hours, chloroform / methanol / acetic acid (20 / 1 / 0.4) shows that the raw material point disappears. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, the residue was repeatedly ground with petroleum ether, and the viscous substance obtained was dissolved in 250ml ethyl acetate, and the 3 Aqueous solution (30ml×5), saturated NaCl aqueous solution (30ml×1), 5% KHSO 4 Aqueous solution (30ml×5), washed...

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Abstract

The invention provides a process for preparing thymopentin Arg-Lys-Asp-Val-Tyr-OH by employing minimum protection strategy, wherein Arg and Tyr whose lateral chain functional groups are not protected are used as raw material. The invention has the advantages of simple process, low cost and easy accessibility of raw material.

Description

technical field [0001] The present invention relates to the preparation method of polypeptide. More specifically, the present invention relates to a preparation method of Arg-Lys-Asp-Val-Tyr-OH. Background technique [0002] Thymopentin is a synthetic pentapeptide active fragment, its sequence corresponds to the 32-36 amino acid residues (Arg-Lys-Asp-Val-Tyr-OH) of thymopoietin, and has important pharmacological effects (Goldstein G, Audhya TK. Thymopoietin to thymopentin: experimental studies. Surv Immunol Res. 1985; 4 Suppl 1:1-10.). It is clinically used for the treatment of various malignant tumors, hepatitis B, infection, autoimmune diseases, type II diabetes, menopausal syndrome, aging and frailty, and decreased immune function. It has the best application prospects in the treatment of malignant tumors and hepatitis B (Gonser S, Weber E, Folkers G. Peptides and polypeptides as modulators of the immune response: thymopentin--an example with u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06
Inventor 彭师奇赵明王超丁文锋林刚
Owner 康哲(湖南)制药有限公司
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