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A liquid-phase synthesis method of tuftsin

A technology for phagocytosing peptide and liquid phase synthesis, which is applied in the field of medicine and chemical industry, can solve the problems of difficult preparation of phagocytic peptide, high production cost, small preparation amount, etc., and achieves easy control of reaction process, low cost and improved synthesis scale. Effect

Inactive Publication Date: 2009-10-07
HANGZHOU HUAJIN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention aims at the problems of difficulty in preparing phagocytosis-promoting peptides by traditional methods, small production amount, low yield and high production cost in the existing solid-phase synthesis technology, and provides a phagocytosis-promoting peptide with large production capacity and relatively low production cost. Liquid Phase Synthesis of Phagocytic Peptides

Method used

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Embodiment Construction

[0035] An embodiment of the present invention is provided below, wherein the reagent dosage and method described can not limit the present invention.

[0036] Substantive content of the invention.

[0037] 1) Amino acid protection

[0038] a. Synthesis of Z-Thr-OH:

[0039]Put 10g of threonine in a 250ml three-necked flask, add 40ml of 2mol / L NaOH solution, and when cooled to -1°C, add 14.6ml of Cbz-CL dropwise, and finish adding in 30min. During the reaction, use 2mol / L sodium hydroxide solution Adjust the pH to keep it at 8-9, continue to stir and react for 2 hours, extract the reaction solution 3 times with ether, remove unreacted Cbz-CL, and acidify the water layer to pH 2 with 1mol / L HCL in an ice bath, that is, a white oil The product was separated out, extracted with ether three times, the ether layers were combined, washed with 5% aqueous sodium chloride until neutral, dried over anhydrous sodium sulfate, and evaporated to dryness of ether to obtain 18.2 g of Z-Thr-O...

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Abstract

The invention relates to a synthetic method of tuftsin (L-Thr-L-Lys-L-Pro-L-Arg-OH). Each alpha-amino group of tuftsin the constituent amino acids is proceeded Z protection, the side chain amino groups uses BOC and pbf protection strategy, condensing by DCC, applying ester activating method to connect peptide from C terminal to N terminal in turns, and at last stripping protecting group from products Z-Thr-Lys(BOC)-Pro_arg(pbf)-OH to obtain the tuftsin Thr-Lys-Pro-Arg-OH. The invention can synthesize numerous tuftsin of high purity with simple processing steps, high yield, low cost and important application value.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to a liquid-phase synthesis method of a phagocytic peptide. Background technique [0002] Phagocytic peptide is a naturally occurring tetrapeptide in the body, with a molecular weight of 500.59, located at residues 289-292 of the CH2 region of the Fc segment of γ-globulin. Tuftsin was discovered by Najjar and Nishioka in 1970 while studying immunoglobulin IgG at Tufts University in the United States. The release of phagocytic peptide requires leukocyte membraneenzyme and endocarboxypeptidase, which can cut the peptide bond connected to the N-terminal and C-terminal of 'phagocytic peptide' in the spleen to release it . The 'phagocytic peptide' in the body must be in a free state to be biologically active. At present, it has been reported that in vitro experiments, phagocytosis-promoting peptides can enhance the killing effect of MΦ, natural kille...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/103C07K1/06C07K1/02
CPCY02P20/55
Inventor 施明珠高留根周正兵俞保彬周天琼
Owner HANGZHOU HUAJIN PHARMA
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