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Photosensitive functionalized solid-supported phase, preparation method and application thereof

A functionalized, light-sensitive technology that can be used in biochemical equipment and methods, chemical instruments and methods, preparation of organic compounds, etc., and can solve problems such as reduced yields of oligomers

Inactive Publication Date: 2012-10-03
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its disadvantage is that although it is relatively stable during the synthesis of oligomers, if it is handled improperly, some Fmoc protecting groups will be removed, so that the free amino groups will react with the acetic anhydride used in the blocking step of the synthesis cycle, and it is expected that the oligomerization product yield decrease

Method used

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  • Photosensitive functionalized solid-supported phase, preparation method and application thereof
  • Photosensitive functionalized solid-supported phase, preparation method and application thereof
  • Photosensitive functionalized solid-supported phase, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1 Preparation of 2-amino-1-(2-nitrophenyl)ethanol (compound 9)

[0051] o-Nitroacetophenone (5.00g, 30.3mmol), CuBr 2 (12.8g, 62.0mmol) was dissolved in a mixed solvent of chloroform (15mL) and ethyl acetate (10mL), heated to reflux at 80°C, and 2 drops of Br 2 Continue to react for 2 hours, add ethyl acetate (50mL) to dilute the system, wash with water (3×80mL), dry over anhydrous sodium sulfate, concentrate the organic phase, dissolve the residue in acetone (15mL), ice-bath, slowly add NaN 3 (2.36g, 36.4mmol), after the addition was completed, it was gradually raised to room temperature, and after the reaction was continued for 1 hour, ethyl acetate was added to dilute, the mother liquor was filtered and concentrated, and the residue was dissolved in methanol (10mL) and dioxane (5mL). Mixed solvent, ice bath and stirring, NaBH 4 (1.14g, 30.0mmol) was dissolved in dioxane (5mL) and added dropwise to the above system. After 10 minutes, the reaction was stopped...

Embodiment 2

[0052] Example 2 Preparation of 6-[two(4-methoxyphenyl)(phenyl)methoxy]hexanoic acid triethylamine (compound 10)

[0053] In anhydrous environment, to DMTr-Cl (two (4-methoxyphenyl) (phenyl) methyl chloride; also known as: 4,4-bismethoxytrityl chloride, 4,4- Dimethoxytrityl chloride) (500 mg, 1.48 mmol) in dichloromethane (10 mL) was added with ethyl 6-hydroxyhexanoate (200 μL, 1.23 mmol) and triethylamine (TEA) (430 μL, 3.08 mmol). The system was stirred at room temperature for 1 hour and then washed with NaHCO 3 Aqueous extraction (0.1M, 2×30mL), dried over anhydrous sodium sulfate. The organic phase was concentrated, and the residue was dissolved in aqueous NaOH (6M, 25 mL) and ethanol (4 mL), stirred at room temperature until the disappearance of the esters as monitored by TLC (thin layer chromatography). The system was diluted with chloroform (50 mL), washed with water (3×50 mL). The organic phase was concentrated and separated on a silica gel column. The ratio of mobi...

Embodiment 3

[0054] Example 3 Preparation of N-[2-hydroxyl-2-(2-nitrophenyl) ethyl] 4-yne butyramide (compound 11a)

[0055]4-Ynebutanoic acid (640mg, 6.51mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC-HCl) (1.24g, 6.47mmol) and 1- Hydroxybenzotriazole (HOBt) (996mg, 6.50mmol) was dissolved in dimethylformamide (DMF) (5mL), and after stirring at room temperature for 1 hour, compound 9 (988mg, 5.40mmol) in DMF ( 3mL) solution. The system was stirred at room temperature for 3 hours, diluted with ethyl acetate (50 mL), washed with water (3×50 mL), dried over anhydrous sodium sulfate. The organic phase was concentrated and separated on a silica gel column with a mobile phase petroleum ether / ethyl acetate ratio of 1 / 1 to obtain compound 11a: light yellow oily liquid (1.13g, 4.31mmol, 80% yield). 1 H NMR (400MHz, CDCl 3 )δ=7.95(m,2H),7.67(m,1H,J=8Hz),7.45(m,1H,J=1,8Hz),6.22(s,1H),5.38(t,1H,J=4Hz ),3.70(dd,2H,J=5,6Hz).2.55(m,2H,J=2Hz),2.46(m,2H,J=2Hz),2.02(m,1H,J=3Hz)....

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Abstract

The invention discloses a photosensitive functionalized solid-supported phase, a preparation method and application thereof. The invention first provides photosensitive functionalized compounds with a structural formula of I or II. Further, the compound with the structural formula of I or II provided by the invention is connected onto amino solid-phase to obtain the photosensitive functionalized solid-supported phase with a structural formula of III or IV. In the solid-phase synthesis of oligonucleotides, the photosensitive functionalized solid-supported phase can be used as 3' end of ODN of the oligonucleotide. After the synthesis process, the oligonucleotides can be cleaved from the solid-supported phase and removed protective groups effectively under illumination to expose the corresponding functional groups, which can be connected with small molecule dyes, or cyclic oligonucleotides are formed through products with double-modified two ends themselves. Results of loading rate and photo-cleavage efficiency experiments show that the compounds with the structural formula of III or IV have higher loading rates and excellent photo-cleavage cutting efficiencies and can be used for solid-phase synthesis and functionalization of the oligonucleotides.

Description

technical field [0001] The invention relates to a functionalized solid phase of oligonucleotides, in particular to a light-sensitive functionalized compound and a light-sensitive functionalized solid phase prepared by using the compound and a preparation method thereof. The invention also relates to the light-sensitive functionalized solid phase The application of the functionalized solid-support phase in the solid-phase synthesis and functionalization of oligonucleotides belongs to the field of solid-phase synthesis and functionalization of oligonucleotides. Background technique [0002] Photoactive groups refer to molecular structures that can undergo chemical changes by forming free radicals or heterocleavage intermediates under photon excitation. It makes it possible to use light to control changes in small molecules or biomacromolecules in complex systems, especially in physiological environments. It is generally believed that compared with other control methods such a...

Claims

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Application Information

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IPC IPC(8): C07C233/20C07C233/38C07C231/12C07C235/10C07C271/12C07C275/20C07C275/64C07C329/06C07C333/04C07D249/04C07H21/00C07H1/00C12Q1/68
CPCY02P20/55
Inventor 汤新景苏蒙
Owner PEKING UNIV
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