A kind of preparation method of 1,4-dithiothreitol

A technology of dithiothreitol and disulfonic acid, which is applied in the fields of mercaptan preparation, sulfonic acid preparation, organic chemistry, etc., can solve problems such as deviation and unsuitable detection of dithiothreitol, and achieve consistent application performance, Simple process and high yield

Active Publication Date: 2022-04-08
SUZHOU YACOO SCI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the reaction process in the above method, due to the limited protection of the dihydroxyl group, the configuration of the product is different from that of the conventional product, and this difference may cause deviations in subsequent applications. Therefore, this method prepares Dithiothreitol is not suitable for all detection situations

Method used

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  • A kind of preparation method of 1,4-dithiothreitol
  • A kind of preparation method of 1,4-dithiothreitol
  • A kind of preparation method of 1,4-dithiothreitol

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preparation example Construction

[0025] The invention provides a kind of preparation method of 1,4-dithiothreitol, comprising the following steps:

[0026] S1: Use 1,4-disulfonic acid-2-butene as the starting material, and oxidize it with an oxidizing agent to obtain the first intermediate; the reaction formula is:

[0027]

[0028] S2: hydrolyzing the first intermediate obtained in step S1 in alkaline solution to obtain the second intermediate; the reaction formula is:

[0029]

[0030] S3: reducing the second intermediate obtained in step S2 with a reducing agent to obtain 1,4-dithiothreitol; the reaction formula is:

[0031]

[0032] Wherein, the molar ratio of the 1,4-disulfonic acid-2-butene to the oxidizing agent is 1:8-13; the molar ratio of the first intermediate to the lye is 0.1-0.2:1.5 -3; the molar ratio of the second intermediate to the reducing agent is 1:6-8; the oxidizing agent is but not limited to one of tungstic acid / hydrogen peroxide and benzoic acid peroxide; the reducing agent ...

Embodiment 1

[0042] A kind of preparation method of 1,4-dithiothreitol comprises the steps:

[0043] In 200ml of dichloromethane, add 15g of 1,4-disulfonic acid-2-butene, control the reaction temperature at 30°C-35°C, add 18g of benzoic acid peroxide in batches, complete the addition within 3 hours, and then control the reaction temperature. Stirring for 16 hours at a temperature higher than 40°C to obtain a reaction solution;

[0044] Add 100ml of NaOH solution (2M) dropwise into the above reaction solution, stir and mix, let stand to separate the liquid, and divide into the first water phase and the first oil phase; then add 100ml of NaOH solution (2M) dropwise to the first oil phase, stir Separation, divided into the second water phase and the second oil phase, combined the first water phase and the second water phase to obtain the total water phase; heated the obtained total water phase to 70°C, reacted for 6h, and cooled down; then added 2g Activated carbon, remove moisture, stir, fi...

Embodiment 2

[0047] A kind of preparation method of 1,4-dithiothreitol comprises the steps:

[0048] In 200ml of dichloromethane, add 15g of 1,4-disulfonic acid-2-butene, control the reaction temperature at 30°C-35°C, add 100ml of tungstic acid / hydrogen peroxide solution in batches (32g of tungstic acid dissolved in 100ml of mass concentration 30% hydrogen peroxide), the addition was completed within 3 hours, and then the reaction temperature was controlled not to be higher than 40°C, and stirred for 16 hours to obtain a reaction solution;

[0049] Add 100ml of NaOH solution (2M) dropwise into the above reaction solution, stir and mix, let stand to separate the liquid, and divide into the first water phase and the first oil phase; then add 100ml of NaOH solution (2M) dropwise to the first oil phase, stir Separation, divided into the second water phase and the second oil phase, combined the first water phase and the second water phase to obtain the total water phase; heated the obtained tot...

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Abstract

The invention discloses a preparation method of 1,4-dithiothreitol, comprising the following steps: taking 1,4-disulfonic acid-2-butene as a starting material, and performing an oxidation reaction with an oxidizing agent to obtain the first an intermediate; hydrolyzing the first intermediate obtained in step S1 in alkaline solution to obtain a second intermediate; reducing the second intermediate obtained in step S2 with a reducing agent to obtain 1,4-di Thiothreitol. The present invention uses 1,4-disulfonic acid-2-butene as starting raw material, the method for synthesizing dithiothreitol through three steps such as oxidation, hydrolysis, reduction, the process of this preparation method is simple and simple, and yield is higher High, the yield is more than 77%, and the obtained product has the same application performance as the conventional product.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 1,4-dithiothreitol. Background technique [0002] Dithiothreitol (DTT) is a small molecule organic reducing agent widely used in cell biology, biochemistry and biomedical applications. Dithiothreitol is highly reductive, largely due to the conformational stability of its six-membered ring in its oxidized state. The typical reduction of disulfide bonds is composed of two consecutive thiol-disulfide bond exchange reactions, but its reducing ability is affected by the pH value, and it can only play a reducing role when the pH value is greater than 7. [0003] Dithiothreitol is often used to reduce the disulfide bonds of protein molecules and polypeptides. It is usually used as a protein sulfhydryl protective agent in vaccine preparations to prevent protein cysteine ​​residues from forming intramolecular and intermolecular disulfide bonds. In the p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/02C07C321/14
CPCC07C319/02C07C303/22C07D303/34C07D301/12C07D301/14C07C321/14C07C309/08
Inventor 曹丽辉袁永坤张振峰
Owner SUZHOU YACOO SCI CO LTD
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