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Reagent for cutting sulfydryl-containing peptides from resins and cutting method

A thiol polypeptide and peptide-cutting reagent technology is applied in the field of reagents for cutting thiol-containing peptides from resins, which can solve the problems of high price and foul odor, and achieve the effects of high price, reduction of three wastes, and reduction of environmental pollution.

Active Publication Date: 2011-02-09
SHANGHAI SOHO YIMING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, when these thiol-containing polypeptides are cut off from the resin, most of the "peptide cutting reagents" used are TFA / EDT / TIS / H 2 O and other mixed solutions (referred to as EDT cut peptide), wherein EDT (Chinese name: ethanedithiol) is a chemical reagent without domestic production, which is expensive and has a foul smell during the reaction.

Method used

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  • Reagent for cutting sulfydryl-containing peptides from resins and cutting method
  • Reagent for cutting sulfydryl-containing peptides from resins and cutting method
  • Reagent for cutting sulfydryl-containing peptides from resins and cutting method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] 1g of octreotide resin containing protective groups {D-Phe-Cys(Trt)-Phe-D-Trp-Lys(Boc)-Thr(tBu)-Cys(Trt)-Th(tBu)-ol-resin, degree of substitution 0.404mmol / g, provided by Shanghai Xuxin Chemical Technology Co., Ltd.}, added to the peptide cutting reagent {trifluoroacetic acid 9.0ml, triisopropylsilane 4ml, mercaptopropionic acid 3ml, phenol 2ml, water 1ml cooled to 5 °C }, at room temperature, magnetically stirred for 1 hour. Filter under reduced pressure with a sand core funnel, and wash the resin twice with 5 ml of trifluoroacetic acid. The resin was discarded, the mother liquor and the washing solution were combined, 80ml of cold diethyl ether was added, and after standing at 5°C for 1.5 hours, a white precipitate precipitated out. The white precipitate was collected by filtration, and the precipitate was repeatedly washed five times with 10 ml of anhydrous ether. Drained, and dried to constant weight under a vacuum environment of phosphorus pentoxide to obtain 410 ...

Embodiment 2

[0053] 1g of somatostatin peptide resin {Ala-Gly-Cys(Trt)-Lys(Boc)-Asn(Trt)-Phe-Phe-Trp-Lys(Boc)-Thr(tBu)-Phe-Thr (tBu)-Ser(tBu)-Cys(Trt)-resin, the degree of substitution is 0.312mmol / g, provided by Shanghai Xuxin Chemical Technology Co., Ltd}, add the peptide cutting reagent {trifluoroacetic acid 9.0ml, cooled to 5 °C, Triisopropylsilane 4ml, sodium mercaptopropionate 3ml, phenol 2ml, water 1ml}, at room temperature, magnetically stirred for 2 hours. Filter under reduced pressure with a sand core funnel, and wash the resin twice with 5 ml of trifluoroacetic acid. Discard the resin, combine the mother liquor with the washing solution, add about 80ml of cold diethyl ether, and let it stand at 7°C for 0.5 hours, a white precipitate precipitates out; collect the white precipitate by filtration, wash the precipitate with 10ml of anhydrous ether five times, and drain it. Phosphorus oxide was vacuum-dried to constant weight to obtain 510 mg (0.311 mmol) of the crude product of red...

Embodiment 3

[0056] 1g of eptifibatide resin {Mpa(Trt)-Har(Pbf)-Gly-Asp(OtBu)-Trp-Pro-Cys(Trt)-resin containing protective groups, with a degree of substitution of 0.560mmol / g, Shanghai Xu Provided by New Chemical Technology Co., Ltd.}, add peptide cutting reagent {trifluoroacetic acid 9.0ml, triisopropylsilane 4ml, thioglycolic acid 3ml, phenol 2ml, water 1ml} cooled to 5°C, and stir magnetically for 3 hours at room temperature. Filter under reduced pressure with a sand core funnel, and wash the resin twice with 5 ml of trifluoroacetic acid. Discard the resin, combine the mother liquor with the washing solution, add 80ml of cold diethyl ether, and let it stand at 5°C for 1 hour, a white precipitate precipitates out; collect the precipitate by filtration, wash the precipitate with 10ml of anhydrous ether repeatedly five times, drain it, and dry it with diethyl ether Phosphorus was vacuum-dried to obtain 466 mg (0.558 mmol) of the crude product of reduced eptifibatide, the yield of cleaved ...

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Abstract

The invention relates to a reagent for cutting peptides, in particular to a reagent for cutting sulfydryl-containing peptides from resins. In addition, the invention also relates to a method for cutting sulfydryl-containing polypeptides from resins, which is suitable for industrial production of sulfydryl-containing polypeptides. The reagent for cutting sulfydryl-containing polypeptides from resins comprises the following components in parts by weight: 85-95 parts of trifluoroacetic acid, 1-5 parts of triisopropylsilane, 1-4 parts of mercaptoundecanoic acid, 1-4 parts of phenol and 1-2 parts of water. The invention has the advantages that because ethanedithiol is a chemical reagent which is not produced at home, the cost of the ethanedithiol is expensive, and the ethanedithiol has effluvial smell in the reaction process; in the invention, mercaptopropionic acid is used for replacing the conventional ethanedithiol, thus the production cost can be lowered, the environment pollution is greatly reduced, and simultaneously, the effect of the peptide cutting reaction can also be improved; and meanwhile, the invention has the characteristics of low procurement cost, reduction of the three wastes, good crude peptide quality and the like, and is very suitable for industrial production of sulfydryl-containing polypeptides.

Description

technical field [0001] The present invention relates to a peptide-cutting reagent, specifically a reagent for cutting off a thiol-containing peptide from a resin; in addition, the present invention also relates to a method for cutting off a thiol-containing polypeptide from a resin. This method is suitable for Industrial production of thiol polypeptides. Background technique [0002] Currently, peptide synthesis is mainly divided into chemical synthesis and enzymatic peptide bond synthesis. Chemical synthesis is further divided into liquid-phase peptide synthesis and solid-phase peptide synthesis. In recent years, solid-phase peptide synthesis has dominated, mainly due to the use of separation techniques such as washing and filtration to purify reaction intermediates and final products. Traditional liquid-phase peptide synthesis is cumbersome and time-consuming, while solid-phase peptide synthesis has attracted more and more attention as a mature technology. [0003] Soli...

Claims

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Application Information

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IPC IPC(8): C07K1/00
Inventor 周又佳
Owner SHANGHAI SOHO YIMING PHARMA
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