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Methyl propenyl phosphoramidite monomer and synthetic method thereof

A technology of methacryl phosphoramidite and synthesis method, which is applied in the field of hydrogel, can solve the problems of difficult purification of chemically cross-linked DNA hydrogel, and achieve the effects of cheap synthetic raw materials, high polymerization efficiency, and high purification efficiency

Active Publication Date: 2014-05-28
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a methacryl phosphoramidite monomer and its synthesis method for the existing chemically cross-linked DNA hydrogel preparation and difficult purification problems

Method used

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  • Methyl propenyl phosphoramidite monomer and synthetic method thereof
  • Methyl propenyl phosphoramidite monomer and synthetic method thereof
  • Methyl propenyl phosphoramidite monomer and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1 Synthesis of methacryl phosphoramidite monomer. Proceed as follows:

[0030] Step 1: Synthesis of intermediate product 2, the route is as follows:

[0031]

[0032] In a round bottom flask, add methacrylic acid (176mg, 2mmol), 6-Amino-2-hydroxymethyl Hexan-1-ol (294mg, 2mmol), DCC (542.4mg, 2.4mmol), HOBt (324mg, 2.4mmol) , 10mL solvent, under the protection of nitrogen, react at room temperature for 24h, after the end, use silica column to separate and purify, NMR and mass spectrum characterization. 1 H NMR (500MHz, CDCl 3 )δ5.67(s,1H),5.32(s,1H),3.78(q,2H),3.67(q,2H),3.35(q,4H),1.96(s,3H),1.70(m,1H ),1.56(m,2H),1.37(m,4H).ESI-MS Calculated for C 11 h 21 NO 3 Na:238.29([M+Na] + ), Found: 238.7.

[0033] Step 2: Synthesis of intermediate product 3, the synthetic route is as follows:

[0034]

[0035]In a round bottom flask was added 2 (270mg, 1.17mmol), 4-dimethylaminopyridine (14mg, 0.117mmol), 7mL pyridine, under nitrogen protection. At th...

Embodiment 2

[0039] Example 2 Synthesis and purification of nucleic acid molecules modified with methacrylic groups.

[0040] Using ordinary CPG as a solid phase carrier, using DNA monomer bases as raw materials, synthesize DNA sequence strand A from the 3' end to the 5' end on a DNA synthesizer, and finally modify the methacrylphosphoramidite monomer at the 5' end body. The specific synthetic sequence is as follows: 5'-X AAA ATC ACA GAT GAG T-3', wherein x is the product 4. After the synthesis, transfer the above CPG to a 2ml clean and sterilized Eppendorf tube, add 0.4mL of methylamine:ammonia water=1:1 solution, ammonolysis at 65°C for 30min, and cut the DNA from the CPG. After ammonium hydrolysis, extract the supernatant, wash the CPG with a small amount of ultrapure water, and combine the supernatant. Add 2.5 times the volume of frozen absolute ethanol and 0.1 times the volume of 3mol / L NaCl to the system, and carry out alcohol precipitation in a -20°C refrigerator. After the ethan...

Embodiment 3

[0041] Example 3 Preparation of linear high molecular weight DNA polymer.

[0042] Dissolve the isolated and purified strand A in ultrapure water to prepare a DNA aqueous solution. Prepare 10% ammonium persulfate and 5% N,N,N,N-tetramethylethylenediamine (TEMED), respectively, that is, dissolve 0.05g ammonium persulfate into 0.5ml ultrapure water and 25μl TEMED into 0.5ml Ultra-pure water. Prepare a mixture of DNA with a final concentration of 1 mM and acrylamide with a final concentration of 4%, and put it in a vacuum desiccator to vacuum and degas for 10 min. Add freshly prepared initiator (ammonium persulfate) and accelerator (TEMED) with a final concentration of 1.4%, mix well, place the reaction system in a vacuum desiccator, and react under vacuum for 15 minutes at room temperature to obtain the strand A linear High molecular DNA polymer.

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Abstract

The invention relates to a methyl propenyl phosphoramidite monomer and a synthetic method thereof, and relates to a hydrogel. The molecular formula of the methyl propenyl phosphoramidite monomer is C(38+n1)H(50+2n1)N3O6P, wherein n1 is the number of CH2 groups, and n1=1-3. The synthetic method comprises the following steps: firstly preparing acrylic-OH2; then preparing acylic-DMT (Dimethyl Terephthalate); finally mixing the acylic-DMT and N,N-diisopropyl ethyl amine in the presence of nitrogen, then dissolving by using dichloromethane, then adding 2-cyanoethyl N,N-diisopropyl chloro phosphoramidite for reaction, and then carrying out column chromatography isolation by using silica gel to obtain the methyl propenyl phosphoramidite monomer. The methyl propenyl phosphoramidite monomer disclosed by the invention is low-cost in synthetic raw material and simple and feasible in step and can obtain higher polymerization efficiency by being higher in purification efficiency after being synthesized into DNA (Deoxyribonucleic Acid); the methyl propenyl phosphoramidite monomer disclosed by the invention can be embedded into any position of a DNA sequence.

Description

technical field [0001] The invention relates to a hydrogel, in particular to a methacryl phosphoramidite monomer and a synthesis method thereof. Background technique [0002] Hydrogel is a kind of hydrophilic polymer, which can swell in water environment and is formed by physical cross-linking or chemical cross-linking. The gel structure can respond to a variety of environmental parameters, such as temperature, pH, ionic strength, and solvent composition, and react accordingly, so it is also called "smart hydrogel". As a new type of material that responds to targets and external stimuli, smart hydrogels have been widely used in the controllable delivery of drugs, the construction of tissue engineering frameworks, the power source of micro-devices, and the application of biosensors. Among them, DNA cross-linked hydrogel is a hydrogel formed by assembling nucleic acid sequences of different units through physical or chemical interactions based on complementary pairing between...

Claims

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Application Information

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IPC IPC(8): C07F9/141C07H21/04C07H1/00C08F290/00C08F220/56C12Q1/68
Inventor 杨朝勇张惠敏马艳丽朱志
Owner XIAMEN UNIV
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