Formula and application of xylene solvent for improving solid phase synthesis efficiency of polypeptide

A peptide solid-phase synthesis and xylene technology, which is applied in the preparation methods of peptides, peptides, chemical instruments and methods, etc., can solve the problems of accelerated peptide synthesis, shortened reaction time, less easy purification, etc., to reduce the steric hindrance effect. , the effect of shortening the reaction time and speeding up the synthesis speed

Inactive Publication Date: 2010-11-10
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a xylene solvent formulation that improves the efficiency of solid-phase synthesis of polypeptides, aiming at overcoming the shortcomings of the existing synthesis methods, such as long time and low yield. The steric hindrance effect caused by internal aggregation shortens the reaction time, speeds up the synthesis of peptides, increases the yield of peptides, and is easy to purify with less impurities, thereby improving the efficiency of synthesizing peptides and reducing the cost of synthesizing peptides

Method used

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  • Formula and application of xylene solvent for improving solid phase synthesis efficiency of polypeptide
  • Formula and application of xylene solvent for improving solid phase synthesis efficiency of polypeptide
  • Formula and application of xylene solvent for improving solid phase synthesis efficiency of polypeptide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Solvent formula: dimethylformamide (DMF) / dichloromethane (DCM) / xylene (DMB)=1 / 2 / 0.25

[0019] Such as Figure 1-4 As shown, in the synthesis of the antimicrobial peptide V13K, this formula was used as a solvent for the peptide grafting reaction. After testing, the connection time of the 7th to 16th amino acids of V13K was shortened to 3-4 hours, and the connection time of the 9th histidine was shortened to 3-4 hours. For 8 hours, the yield of pure product was 25-35mg / 0.1mmol resin. Under the same conditions, using traditional common solvents, the 7th to 16th amino acid of V13K was connected for more than 10 hours, and the 9th histidine was connected for more than 20 hours, and the yield of pure product was 7-9mg / 0.1mmol resin .

[0020] The list of raw materials adopted in the embodiment and the foregoing process is as follows:

[0021] no

Raw material and trial product name

source

1

Rink amide MBHA resin

Tianjin Hecheng Technology Co...

Embodiment 2

[0039] The formula of dimethylformamide (DMF) / dichloromethane (DCM) / xylene (DMB) = 1 / 2 / 0.5 was used as the solvent for the peptide grafting reaction. After testing, the connection time of the 7th to 16th amino acids of V13K shorten to 4-5 hours, wherein the 9th histidine connection time is 5 hours.

[0040] Specific steps are as follows:

[0041]The decapping reagent is: hexahydropyridine:DMF=1:4, volume ratio;

[0042] Said peptide-connecting solvent is: DMF: DCM: DMB=1: 2: 0.5, volume ratio; in the peptide-connecting reagent, the number of moles of HBTU is 4.5 times that of the raw material resin, and the number of moles of HOBt is 3.5 times that of the raw material resin .

[0043] Said ninhydrin detection reagent is: solution A, ninhydrin:ethanol=5:100, mass volume ratio. Solution B, phenol:ethanol=80:20, volume ratio. Solution C, 0.001M potassium cyanide aqueous solution:pyridine=1:49, volume ratio.

[0044] (1) Take 125mg Rink amide MBHA resin (0.8mmol / g resin, 0.1m...

Embodiment 3

[0055] The formula of dimethylformamide (DMF) / dichloromethane (DCM) / xylene (DMB) = 1 / 1.5 / 0.5 was used as the solvent for the peptide grafting reaction. After testing, the connection time of the 7th to 16th amino acids of V13K Reduced to 3-5 hours.

[0056] Specific steps are as follows:

[0057] The decapping reagent is: hexahydropyridine:DMF=1:4, volume ratio;

[0058] Said peptide-connecting solvent is: DMF: DCM: DMB=1: 1.5: 0.5, volume ratio; in the peptide-connecting reagent, the number of moles of HBTU is 4.5 times that of the raw material resin, and the number of moles of HOBt is 3.5 times that of the raw material resin .

[0059] Said ninhydrin detection reagent is: solution A, ninhydrin:ethanol=5:100, mass volume ratio. Solution B, phenol:ethanol=80:20, volume ratio. Solution C, 0.001M potassium cyanide aqueous solution:pyridine=1:49, volume ratio.

[0060] (1) Take 125mg Rink amide MBHA resin (0.8mmol / g resin, 0.1mmol), soak it in 3ml DCM for 8h, make the resin f...

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Abstract

The invention relates to a formula and application of a xylene solvent for improving solid phase synthesis efficiency of polypeptide, which is characterized in that the formula of the xylene solvent comprises dimethylformamide DMF, dichloromethane DCM and xylene DMB at a volum ratio of 1:1.5-2.5:0.15-1.0. The invention effectively reduces the cost for synthesizing the polypeptide, reduces the steric hindrance effect of hydrophobic lateral chains and blocking groups of amino acid, shortens the reaction time and accelerates the polypeptide synthesizing speed, and the polypeptide has high yield and few impurities.

Description

Technical field: [0001] The invention relates to a xylene solvent formulation and application for improving the efficiency of polypeptide solid-phase synthesis, and belongs to the field of polypeptide solid-phase synthesis. Background technique: [0002] The commonly used method for solid-phase synthesis of peptides is the peptide reaction of activated ester method. The reaction mechanism is a nucleophilic addition-elimination reaction. The deprotected amino group nucleophilically attacks the carbonyl carbon of the amino acid activated ester to form a charged tetrahedral transition state. Elimination of hydroxybenzotriazole to form an amide bond. Since the transition state is charged, according to the solvation effect, a polar solvent is beneficial to the stability of the transition state. The greater the polarity of the solvent, the faster the reaction speed, the weak polar solvent is not conducive to this reaction, so the strong polar N,N-dimethylformamide (DMF) is usuall...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K1/06C07K1/04
Inventor 陈育新毛世忠黄宜兵王笑非潘玲
Owner JILIN UNIV
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