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Sulfur octyl phosphoramido ester and synthetic method and application thereof

A technology of lipoyl ester and phosphoramidite, which is applied in the field of phosphoramidite lipoyl ester and its synthesis, can solve the problems of not being able to meet the needs of scientific research and business, and the lack of disulfide bond-containing terminal reagents, etc., and achieve good results. The effect of commercialization prospects, simplified synthesis workload, good universality and stability

Inactive Publication Date: 2018-02-09
CHINA UNIV OF PETROLEUM (EAST CHINA)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are very few disulfide bond-containing end-group reagents available at present, which cannot meet the growing scientific research and commercial needs.

Method used

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  • Sulfur octyl phosphoramido ester and synthetic method and application thereof
  • Sulfur octyl phosphoramido ester and synthetic method and application thereof
  • Sulfur octyl phosphoramido ester and synthetic method and application thereof

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preparation example Construction

[0037] A method for preparing the above-mentioned phosphoramidite lipoyl ester, comprising the steps of obtaining lipoic acid through reduction reaction to obtain lipoyl alcohol, and then obtaining phosphoramidite lipoyl ester through esterification.

[0038] The preparation method of concrete above-mentioned phosphoramidite lipoyl ester, its reaction process is as shown in reaction formula I:

[0039]

[0040] Reaction I

[0041] Wherein compound II is lipoic acid, compound III is lipoyl alcohol, and compound I is phosphoramidite lipoyl ester.

[0042] In an optional embodiment: the lipoic acid is prepared in anhydrous tetrahydrofuran using sodium trimethoxyborohydride and boric acid as reducing agents to prepare lipoic alcohol.

[0043] In an optional embodiment: the reduction reaction specifically includes the following steps: dissolving sodium trimethoxyborohydride and boric acid in anhydrous tetrahydrofuran, adding lipoic acid while stirring in an ice bath, and stirri...

Embodiment 1

[0059] A kind of synthetic method of phosphoramidite lipoyl ester, comprises the following steps:

[0060] Step 1: Preparation of lipoic alcohol: Dissolve 1.0 g of sodium trimethoxyborohydride and 0.15 g of boric acid in 66 ml of anhydrous tetrahydrofuran, and add a solution of 1.0 g of lipoic acid in 66 ml of anhydrous tetrahydrofuran at one time while stirring in an ice bath , and the reaction solution was stirred at 15° C. for 30 hours. After the reaction was completed, 9 ml of 3M sulfuric acid solution was added dropwise to the reaction solution, and the insoluble matter was filtered off. The filtrate was washed with 100 ml of chloroform and 100 ml of saturated brine, and the organic phase was separated and dried over anhydrous sodium sulfate. The organic phase was rotary evaporated to obtain 1.5 g of lipoctyl alcohol (pale yellow viscous liquid), with a yield of 81%.

[0061] The proton nuclear magnetic resonance spectrum detection result of compound IV in the intermedia...

Embodiment 2

[0073] A kind of synthetic method of phosphoramidite lipoyl ester, comprises the following steps:

[0074] Step 1: Preparation of lipoic alcohol: Dissolve 3.0 g of sodium trimethoxyborohydride and 0.2 g of boric acid in 200 ml of anhydrous tetrahydrofuran, and add a solution of 2.0 g of lipoic acid in 200 ml of anhydrous tetrahydrofuran at one time while stirring in an ice bath , and the reaction solution was stirred at 20° C. for 24 hours. After the reaction, 20 ml of 4M sulfuric acid solution was added dropwise to the reaction solution, and the insoluble matter was filtered off. The filtrate was washed with 200 ml of chloroform and 100 ml of saturated brine, and the organic phase was separated and dried over anhydrous sodium sulfate. The organic phase was rotary evaporated to obtain 1.6 g of lipoyl alcohol (pale yellow viscous liquid), with a yield of 83%.

[0075] The proton nuclear magnetic resonance spectrum detection result of compound IV in the intermediate product thi...

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Abstract

The invention relates to the technical field of chemical synthesis, in particular to thio-octyl phosphoramido ester and a synthetic method and application thereof. The synthetic method of the thio-octyl phosphoramido ester includes the step of: adopting thioctic acid as a raw material, performing a reduction reaction to obtain thio-octanol, and performing an esterification reaction to obtain the thio-octyl phosphoramido ester. When the thio-octyl phosphoramido ester is used as a DNA end-group modifier, DNA with sulfur-containing modified end groups can be prepared efficiently and massively, and the simple and efficient DNA end-group modifier with controllable cost can be provided for sulfur-containing modification of a 5' end of DNA; meanwhile, the synthetic method has the advantages of aconcise path, convenient operation, a simple method for purifying intermediates and the product, and requirements of scientific research and business can be fully met.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a phosphoramidite lipoyl ester and its synthesis method and application. Background technique [0002] Sulfur-modified DNA is of great significance in biological analysis, preparation of smart nanomaterials and molecular biology. Since the maturity of DNA solid-phase synthesis technology in the 1990s, people have developed a variety of sulfur-containing reagents for DNA end group modification, and realized the efficient preparation of end-group sulfur-containing DNA. Among the existing sulfur-containing end group modification reagents, thiol-modified end group reagents account for the majority, and this type of reagent is flexible and has a wide range of applications. However, the thiol in it is easily oxidized to form a disulfide structure, which has poor stability. Moreover, the binding performance of mercapto groups in thiols to noble metal nanoparticles, such as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6553C12N15/10
CPCC07F9/655345C12N15/10
Inventor 孙亚伟程童姬燕云王栋王继乾徐海
Owner CHINA UNIV OF PETROLEUM (EAST CHINA)
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