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Tetravalent platinum complex oxidant and preparation method and application thereof

A complex, tetravalent platinum technology, applied in the field of tetravalent platinum complex oxidant and its preparation, can solve the problems of high reaction system requirements, slow reaction rate, low reaction yield and the like, and achieves fast reaction rate, simple preparation, The effect of simple reaction solvent

Inactive Publication Date: 2017-06-20
HEBEI UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] One of the purposes of the present invention is to provide a tetravalent platinum complex oxidant and its application to solve the problem of slow reaction rate, high requirements on the reaction system and oxidized methionine residues when the existing platinum complex oxidant synthesizes disulfide bonds in polypeptide molecules. The base causes the problem of low reaction yield

Method used

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  • Tetravalent platinum complex oxidant and preparation method and application thereof
  • Tetravalent platinum complex oxidant and preparation method and application thereof
  • Tetravalent platinum complex oxidant and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0058] ①In a 50 mL three-necked flask, add 0.2 g of potassium tetrachloroplatinate and 20 mL of 50 mM hydrochloric acid solution, then add 200 μL of ethylenediamine, magnetically stir, and reflux at 100°C for 15 h; after the reaction is completed, cool to After filtering at room temperature, the resulting solid was washed three times with ethanol, and then dried in vacuum at 50°C for 12 hours to obtain a yellow dichloro(ethylenediamine) platinum complex;

[0059] ② Add 0.1 g dichloro(ethylenediamine) platinum into a 50 mL single-necked bottle, then add 50 mL water, add 0.3 g o-phenanthroline after ultrasonic dispersion, stir, and react at 100 ° C for 50 h; cool down after the reaction to room temperature, filtered, the light yellow filtrate was concentrated to 3-6 mL, and then 100 mL of acetonitrile was added, a light yellow solid precipitated, filtered, the solid was washed with acetonitrile for 3 times, and then vacuum-dried to obtain a light yellow ionic divalent platinum co...

Embodiment 2

[0063] ①In a 50 mL three-necked flask, add 0.2 g of potassium tetrachloroplatinate and 20 mL of 50 mM hydrochloric acid solution, then add 200 μL of ethylenediamine, magnetically stir, and reflux at 100°C for 12 h; after the reaction is completed, cool to After filtering at room temperature, the obtained solid was washed with ethanol three times, and then dried in vacuum at 50°C for 12 hours to obtain a yellow dichloro(ethylenediamine) platinum complex;

[0064] ② Add 0.2 g of dichloro(ethylenediamine) platinum into a 50 mL single-necked bottle, then add 100 mL of water, add 0.5 g of 2,2′-bipyridine after ultrasonic dispersion, stir, and react at 100°C for 72 h After the reaction is completed, cool to room temperature, filter, and concentrate the light yellow filtrate to 3-5 mL, then add 80 mL of acetonitrile, a light yellow solid precipitates, filter, wash the solid 3 times with acetonitrile, and then dry in vacuo to obtain light yellow ionic di Valence platinum complexes;

...

Embodiment 3

[0068] The oxidizing agent prepared in the present invention (that is, the tetravalent platinum complex) can react with various reduced polypeptides containing sulfhydryl groups to synthesize disulfide bonds in polypeptide molecules.

[0069] Using the tetravalent platinum complex prepared in Example 1 and Example 2 and the reduced polypeptide containing sulfhydryl group to synthesize intramolecular disulfide bonds of the polypeptide through the following scheme: react the tetravalent platinum complex with the reduced polypeptide solution at room temperature for 1 ~5min; after the reaction, the reaction product was separated by high performance liquid chromatography, and the reaction product was identified by mass spectrometry.

[0070] The oxidizing agent of the present invention can oxidize a variety of reduced polypeptides containing two sulfhydryl groups. These polypeptides are synthesized by the traditional solid-phase polypeptide synthesis method. The polypeptide, the ob...

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Abstract

The invention discloses a tetravalent platinum complex oxidant and a preparation method and application thereof in synthesizing of disulfide bonds in a polypeptide molecule. The tetravalent platinum complex oxidant has a structure shown in the formula (I), wherein n is 0 or 2; X is halide ion with -1 valence. The preparation method of the tetravalent platinum complex oxidant comprises the following steps of enabling potassium chloroplatinite and ethylenediamine dihydrochloride to react, so as to obtain dichloro(ethylenediamine)platinum; enabling the dichloro(ethylenediamine)platinum and a heteroaromatic ring containing two nitrogen atoms to react, so as to obtain an ion type bivalent platinum complex; enabling the ion type bivalent platinum complex and a hydrochloric acid solution containing hydrogen peroxide to oxidize, so as to obtain the tetravalent platinum complex oxidant. The tetravalent platinum complex oxidant has the advantages that the residual radicals of methionine are not oxidized, the reaction yield rate is high, the reaction rate in the stronger acid reaction medium is quick, and the cost for synthesizing the disulfide bonds in a pharmaceutical molecule by using the oxidant is greatly reduced.

Description

technical field [0001] The invention relates to a complex oxidant, specifically a tetravalent platinum complex oxidant and its preparation method and application. Background technique [0002] Polypeptide drugs containing intramolecular disulfide bonds have been used in the treatment of various diseases. In the synthesis process of polypeptide drugs containing intramolecular disulfide bonds, the synthesis of intramolecular disulfide bonds in polypeptides is a key step. At the same time, The synthesis of intramolecular disulfide bonds of polypeptide drugs is an important reaction in fine organic chemical industry and medicinal chemistry. At present, the oxidation methods are generally divided into two categories: (1) heterogeneous oxidation reaction between solid and liquid to generate intramolecular disulfide bonds of polypeptides ; (2) Homogeneous oxidation in solution to synthesize intramolecular disulfide bonds of polypeptides. Among them, homogeneous oxidation reaction ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C07K7/16C07K7/06C07K1/02C07K1/20
CPCC07F15/0093C07K7/06C07K7/16
Inventor 霍树营宋常英赵晓伟侯晓男申世刚
Owner HEBEI UNIVERSITY
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