Nucleic acid containing photosensitive unit, preparation method and application thereof

A photosensitive unit and nucleic acid technology, which is applied in the preparation of sugar derivatives, chemical instruments and methods, organic chemistry, etc., can solve the problems of cumbersome operation, poor efficiency, and mild reaction, and achieve convenient operation, simplified methods, and reduced preparation costs Effect

Inactive Publication Date: 2019-06-14
CHINA UNIV OF PETROLEUM (EAST CHINA)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The invention proposes a nucleic acid containing a photosensitive unit, its preparation method and its application, which solves the technical problems of cumbersome operation, mild reaction and poor efficiency in the synthesis of the existing light-responsive nucleic acid terminal thiol reagent

Method used

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  • Nucleic acid containing photosensitive unit, preparation method and application thereof
  • Nucleic acid containing photosensitive unit, preparation method and application thereof
  • Nucleic acid containing photosensitive unit, preparation method and application thereof

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preparation example Construction

[0036] An embodiment of the present invention provides a method for preparing a nucleic acid containing a photosensitive unit according to the above embodiments, comprising the following steps:

[0037] S1: Preparation of sulfur-containing phosphoroimide ester: starting from n-mercapto-1-alkanol, it was mixed with 4,5-dimethoxy-2-nitrophenyl-ethyl chloride Under the action of an organic base, the reaction generates n-(4,5-dimethoxy-2-nitrophenyl)-ethylsulfide-1-alkanol, which is then combined with 2-cyanoethyl-N, N-diisopropyl phosphoramidite chloride reacts under the action of an organic base to generate n-(4,5-dimethoxy-2-nitrophenyl)-ethylsulfide-1-(2-cyano Ethyl-N,N-diisopropylphosphoramidite alkyl alcohol ester) to obtain sulfur-containing phosphoramidite;

[0038] In this step, the obtained sulfur-containing phosphoramidite has a structural formula as shown in formula (II):

[0039]

[0040] Wherein, the range of n value is 1-15.

[0041]S2: Preparation of nucleic ...

Embodiment 1

[0065] The preparation method of sulfur-containing phosphoramidite comprises the following steps:

[0066] Step 1: Preparation of 4,5-dimethoxy-2-nitrophenyl-ethyl chloride

[0067] 50 mg of ferric chloride hexahydrate was dispersed in 200 ml of ethanol, and 1.0 g of powdered activated carbon was added at one time under stirring in an ice bath, and stirred at room temperature for 2 hours. Subsequently, 10 ml of 35% hydrazine hydrate and 4.0 g of 4,5-dimethoxy-2-nitroacetophenone were added, the reaction solution was stirred at room temperature for 1 hour, and 20 ml of 1M hydrochloric acid solution was added dropwise thereto, and the insoluble thing. After the filtrate was concentrated, it was redissolved in 50 ml of ethyl acetate, washed with 200 ml of saturated brine, and the organic phase was separated and dried over anhydrous sodium sulfate. The organic phase was rotary evaporated to obtain 4.0 g of (4,5-dimethoxy-2-nitrophenyl)-ethanol (light yellow solid), with a yield ...

Embodiment 2

[0080] A method for preparing a nucleic acid containing a photosensitive unit, comprising the following steps:

[0081] Step 1: Take 700 mg of 6-(4,5-dimethoxy-2-nitrophenyl)-ethylsulfide-1-(2-O-cyanoethyl-N,N-diisopropyl Phosphoramidite hexanol ester) was dissolved in 10 ml of anhydrous acetonitrile, and transferred to the end group modification reagent bottle of ABI 394 nucleic acid synthesizer under nitrogen protection. Input nucleic acid sequence: 5'CCT AGA TTC AGT TCA ACT TA 3', use DMT-retained synthesis mode, and perform synthesis on the order of 1 μmol.

[0082] Step 2: After the synthesis, the solid phase carrier is taken out, dispersed in 1 ml of 5%-32% methylammonia aqueous solution, heated at 55-75°C for 1-4 hours, centrifuged to remove insoluble matter, and the solution is concentrated to obtain the crude product . The target product was separated by high performance liquid chromatography and characterized by MALDI-TOF for structural information.

[0083] The p...

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Abstract

The invention provides a nucleic acid containing a photosensitive unit, a preparation method and an application thereof, which belong to the technical filed of chemical synthesis, and can solve the technical problems that the operation of the existing photoresponsive nucleic acid end group sulfhydrylation reagents is complex, the reaction is not mild, and the efficiency is poor. The nucleic acid containing the photosensitive unit provided by the technical scheme is as shown in a formula (I): wherein a value of n ranges from 1 to 15. The nucleic acid can be applied to the preparation of a thiolend group modifying reagent.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a nucleic acid containing a photosensitive unit, its preparation method and its application. Background technique [0002] Sulfhydryl-modified nucleic acids (DNA, RNA and various other artificial nucleic acids) are of great significance in the preparation of biological probes, design of biological materials, chemical biology and molecular biology. With the maturity of nucleic acid synthesis technology and the commercialization of automatic nucleic acid synthesizers, people have developed a variety of thiol reagents that can be used for the modification of nucleic acid end groups, realizing the large-scale preparation of end-group sulfur-containing nucleic acids. [0003] Since the thiol group cannot be exposed in solid-phase synthesis, people need to protect the thiol group. At present, the thiol-modified terminal reagents mostly use trityl (Trit) or 4,4-di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/10C07H1/00C07H21/04
Inventor 孙亚伟程童吕环芳孙立梅夏宁远王栋王继乾
Owner CHINA UNIV OF PETROLEUM (EAST CHINA)
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