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Deoxyribonucleic acid (DNA) base analogue with photo-crosslinking group biaziridine and synthetic method thereof

A technology of photocrosslinking group and diaziridine, which is applied in the field of DNA base analogs and their synthesis, can solve the sites where the secondary structure is unknown and the interaction between nucleic acid aptamers and proteins is the strongest. and other problems, to achieve the effect of simple and feasible steps and cheap synthetic raw materials

Active Publication Date: 2013-12-11
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although nucleic acid aptamers can specifically bind to the target protein, they do not know what the secondary structure of the nucleic acid aptamer interacts with the protein, nor do they know which nucleic acid aptamer has the strongest ability to interact with the protein. what is the site

Method used

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  • Deoxyribonucleic acid (DNA) base analogue with photo-crosslinking group biaziridine and synthetic method thereof
  • Deoxyribonucleic acid (DNA) base analogue with photo-crosslinking group biaziridine and synthetic method thereof
  • Deoxyribonucleic acid (DNA) base analogue with photo-crosslinking group biaziridine and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The synthesis of intermediate product 2, its synthetic route is as follows:

[0032]

[0033] Add raw material 1 (105.3mg, 0.82mmol), 1-aminohexanediol (132mg, 0.902mmol), DCC (203mg, 0.984mmol), HOBt (133mg, 0.984mmol), 10mL solvent in a round bottom flask, in Under the protection of nitrogen, the reaction was carried out at room temperature for 24 hours. After the completion, it was separated and purified with a silica column, and characterized by NMR and mass spectrometry. 1 H NMR (500MHz, CDCl 3 )δ3.73(m,2H),3.61(m,2H),3.19(m,2H),1.98(t,2H),1.72(t,2H),1.66(m,1H),1.45(m,2H ),1.30-1.20(m,4H),0.99(s,3H).ESI-MS Calculated for C 12 h 23 N 3 o 3 Na:280.33([M+Na] + ), Found: 280.2.

Embodiment 2

[0035] The synthesis of intermediate product 3, its synthetic route is as follows:

[0036]

[0037] In a round bottom flask was added 2 (424.4mg, 1.65mmol), 4-dimethylaminopyridine (20mg, 0.165mmol), 10mL pyridine, under nitrogen protection. At the same time, under nitrogen protection, 4-4'-dimethoxytriphenylchloromethane (560mg, 1.65mmol) was dissolved in 4mL of dichloromethane, and the solution was added dropwise to the above solution under ice bath, and then After 24 hours of reaction, water was added to the reaction system, and then extracted three times with ethyl acetate, separated and purified by silica column, and characterized by NMR and mass spectrometry. 1 H NMR (500MHz, CDCl 3 )δ7.41-6.82(m,13H),3.79(s,6H),3.67-3.61(m,2H),3.27-3.08(m,4H),2.40(s,1H),1.93(m,2H) ,1.75(m,2H),1.59(s,4H),1.44(m,2H),1.02(s,3H).ESI-MS Calculated for C 33 h 41 N 3 o 5 Na:582.7([M+Na] + ), Found: 582.3.

Embodiment 3

[0039] Synthetic product 4, its synthetic route is as follows:

[0040]

[0041] Add 3 (181.2mg, 0.324mmol) into a round bottom flask, and add 5mL of dichloromethane under nitrogen protection. Add N,N-diisopropylethylamine and 2-cyanoethyl N,N-diisopropylphosphoramidite chloride dropwise under ice bath, react in ice bath for 2h, separate and purify with silica column , NMR and MS characterization, such as figure 1 ,2. 1 H NMR (500MHz, CDCl 3 )δ7.41-6.82(m,13H),3.79(s,6H),3.76-3.5(m,6H),3.27-3.08(m,4H),2.6-2.5(m,4H),1.93(m, 2H),1.85(m,1H),1.72(m,2H),1.4(s,4H),1.2(m,2H),1.15(d,6H),1.12(d,6H),1.02(s,3H ). 31 P NMR (202MHz, CDCl 3 )δ147ppm.ESI-MS Calculated for C 42 h 58 N 5 o 6 PNa:782.9([M+Na] + ), Found: 782.5.

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Abstract

The invention discloses a deoxyribonucleic acid (DNA) base analogue with a photo-crosslinking group biaziridine and a synthetic method thereof, and relates to the DNA base analogue and the synthetic method thereof. The DNA base analogue with the photo-crosslinking group biaziridine is a biaziridine phosphoramidite monomer; an intermediate product with two hydroxyl groups is connected on the basis of a compound 1; a material 1-amino-hexylene glycol is led; an amido bond is formed under condensation of dicyclohexylcarbodiimide and 1-hydroxybenzotriazole, so as to obtain an immediate product 2; the material 4-4'-dimethoxy triphenyl methyl chloride is led; pyridine and dichloromethane are taken as solvents; an immediate product 3 is obtained under catalytic action of 4-dimethylamino-pyridine; the material 2-cyanoethyl N, N-diisopropyl chlorinated phosphoramide is led; N,N-diisopropylethylamine is taken as alkali and a catalyst; dichloromethane is taken as a solvent, so as to obtain the final product under the condition of anaerobic reaction without water.

Description

technical field [0001] The invention relates to a DNA base analog and a synthesis method thereof, in particular to a DNA base analog with a photocrosslinking group diaziridine and a synthesis method thereof. Background technique [0002] Diaziridine is a three-membered heterocyclic structure containing two nitrogen atoms, which can rapidly produce carbene under the irradiation of 365nm ultraviolet light, and the by-product is nitrogen gas. Carbenes are very reactive molecules capable of intercalation reactions with adjacent groups, even C-H bonds. The diaziridine group has high reactivity only under light, and the molecule is very stable under conventional operation, so it is a very advantageous photocrosslinking group. As early as the 1960s, the concept of photoaffinity labeling (PAL) had been proposed, making the application of photocrosslinking groups in biological analysis a research hotspot of scientists. [0003] In the study of the interaction between biomolecules, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/645
Inventor 杨朝勇张惠敏宋彦龄邹远朱志葛韵田中群
Owner XIAMEN UNIV
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