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A kind of industrial preparation method of baadin tripeptide

A technology for cutting peptides and peptide cutting reagents, which is applied to the preparation method of peptides, chemical instruments and methods, peptides, etc., can solve the problems of no production and preparation reports, difficult industrial production, and low yield of peptides, and achieve convenient Effects of industrial implementation, reduction of three wastes, and simplification of process

Active Publication Date: 2016-03-16
SHANGHAI SOHO YIMING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current literature only has reports on research and application, but no reports on its production and preparation
If you refer to the technology disclosed in "Progress in Chemical Industry" No. 2, 2003, 153-156, "Research Progress in Solid Phase Synthesis of Thymopentin", the peptide yield is low, the production cost is high, the process is complicated, and highly toxic hydrogen fluoride is used. and trifluoroacetic acid, the pollution of the three wastes is serious, and it is difficult to carry out industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 1. Preparation of Fmoc-Asp(tBu)-resin

[0033] Take 100g Wang resin (1.5mmol / g resin, 150mmol), soak it in 1000ml DMF to fully swell the resin, and drain it.

[0034] Take 93g of Fmoc-Asp(tBu)-OH (FW: 411.5, 225mmol), 72g of TBTU (FW: 321, 225mmol), 30g of HOBT (FW: 135.1, 225mmol), 50ml of NMM (MW = 101.2), dissolve it in 800ml of DMF, add to the reaction vessel, The peptide inoculation reaction was carried out at 25~27°C for 60 minutes.

[0035] Drain, wash three times with DMF, absolute ethanol and DMF respectively, and drain.

[0036] 2. Preparation of Fmoc-Gly-Asp(tBu)-resin

[0037] Add 1000ml decapping reagent, react for 30 minutes at 25~27℃, drain, wash with DMF, absolute ethanol and DMF three times respectively, and drain.

[0038] Add 67gFmoc-Gly-OH (FW: 297.3, 225mmol), 72gTBTU (FW: 321, 225mmol), 30gHOBT (FW: 135.1, 225mmol), 50mlNMM (MW=101.2), dissolve with 800mlDMF, add to the reaction vessel, 25~27 The peptide grafting reaction was carried out at ℃ f...

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Abstract

The invention discloses an industrialization preparation method for RDG peptide. The technical scheme of the present invention comprises the following steps: Wang resin is taken as an initial raw material and TBTU / HOBt is taken as a condensing agent, amino acid possessing a Fmoc-protective group is successively connected according to a solid phase synthesis method, Boc-Arg-OH.HCl is used by a last amino acid to obtain protective tripeptide resin, and meanwhile crude products are obtained by sequentially removing Fmoc-protective groups synchronized with acellular side-chain protective groups and cutting peptides, and the RDG peptide elaborate products are prepared after the crude products are separated and purified by a C18 high performance liquid phase column and freeze-dried. The method of the invention is capable of reducing the production cost and simplifying the process flow. The crude products can be deposited by ether after cutting peptides so that the usage of hydrogen fluoride with severe toxicity can be avoided and the three wastes pollution is reduced. C18 column is used for separating and purifying to avoid the usage of trifluoroacetic acid and reduce three wastes. The purification yield is more than 50%, the each step of transpeptidase yield is more than 98%, the yield after cutting peptides is 88%, the separation and purification yield is 58% and the overall yield is 51%. The method of the present invention is convenient for industrial enforcement and has large industrialization prospect.

Description

technical field [0001] The present invention relates to a preparation method of regodipeptide (RGD peptide), in particular to a solid-phase polypeptide synthesis method of regodipeptide. Background technique [0002] Chinese name: Snake toad tripeptide [0003] English name: RDG [0004] The structural formula is Arg-Gly-Asp-OH [0005] Molecular formula: C 12 h 22 N 6 o 6 [0006] Molecular weight: 346.3 [0007] CAS number: 99896-85-2 [0008] RGD peptide is a short peptide containing arginine-glycine-aspartic acid (Arg-Gly-Asp-OH), which acts as a recognition site for the interaction between integrins and their ligands, and mediates the interaction between cells and extracellular matrix and cells. interaction between. Snakebain tripeptide is clinically used as an immune enhancer, early treatment of AIDS, chronic hepatitis, malignant tumors, surgery and severe infection, and can also be used for diabetes, rheumatoid arthritis, lupus erythematosus, glomerulonephri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/09C07K1/20C07K1/06C07K1/04
CPCY02P20/55
Inventor 周逸明崔颀蔡华成
Owner SHANGHAI SOHO YIMING PHARMA
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