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Feather weight preparation method of cytosine containing PNA (pentose nucleic acid) monomer

A cytosine, kilogram-level technology, applied in the field of kilogram-level preparation of cytosine-containing PNA monomers, can solve the problems of restricting PNA application research work, small synthesis scale, etc.

Inactive Publication Date: 2014-01-22
SUZHOU VIVOTIDE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, some companies in China can customize and synthesize PNA series products, but their synthesis scale is very small, generally at the milligram level. This situation greatly restricts the application and research work of PNA compounds.

Method used

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  • Feather weight preparation method of cytosine containing PNA (pentose nucleic acid) monomer
  • Feather weight preparation method of cytosine containing PNA (pentose nucleic acid) monomer
  • Feather weight preparation method of cytosine containing PNA (pentose nucleic acid) monomer

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preparation example Construction

[0024] A method for preparing a kilogram-level PNA monomer containing cytosine, comprising the following steps:

[0025] Step 1) Nitrogen alkylation reaction of ethylenediamine and monochloroacetic acid, overnight reaction to obtain N-(2-aminoethyl)glycine;

[0026] Step 2) Using N-(2-aminoethyl)glycine as a raw material, add a mixed solvent of dichloromethane and DMF, add trimethylchlorosilane at room temperature, react for 40 minutes, then cool down to 0-5 degrees and add Fmoc- OSu, NMM is added dropwise at 5 degrees, and the insulation reaction is completed until the raw material is reacted to obtain N-(2-Fmoc-aminoethyl)glycine;

[0027] Step 3) Take N-(2-Fmoc-aminoethyl)glycine as raw material, add methanol, heat thionyl chloride to reflux until the raw material reacts completely, and obtain N-(2-Fmoc-aminoethyl)glycine methyl ester hydrochloride Salt;

[0028] Step 4) using cytosine as a raw material, DMF as a solvent, first adding sodium hydrogen at low temperature fo...

Embodiment 1

[0038] Step 1) Put 500 ml of ethylenediamine into a 1-liter three-necked bottle, cool it in an ice bath to 10 degrees, add 75 grams of chloroacetic acid in batches and control the temperature below 10 degrees, after each batch is added, observe that it is completely consumed before adding more One batch, after the feeding is completed, react overnight at room temperature, spin dry ethylenediamine, recover ethylenediamine for recycling, use an oil pump to remove ethylenediamine as much as possible, and recrystallize with DMSO to obtain white powder crystals, which are N- (2-aminoethyl) glycine, yield 40-50%;

[0039]Step 2) 50 grams of N-(2-aminoethyl) glycine was dissolved in a mixed solution of 850 milliliters of methylene chloride and 50 milliliters of DMF, 134 milliliters (1.05mol) of trimethylchlorosilane was added, and the reaction mixture was stirred at room temperature for 40 Minutes, then cooled to 5 degrees, 134 grams of Fmoc-OSu was added to the above mixture, 186 mi...

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Abstract

The invention discloses a feather weight preparation method of a cytosine containing PNA (pentose nucleic acid) monomer. The feather weight preparation method comprises the following steps: reacting ethanediamine with chloroacetic acid and recrystallizing by using DMSO (dimethylsulfoxide) so as to obtain N-(2-aminoethyl) glycine; using N-(2-aminoethyl) glycine as a reactant, adding raw materials, and reacting so as to obtain N-(2-Fmoc-aminoethyl) glycine methyl ester hydrochloride which serves as an intermediate 1; using cytosine as a reactant, adding raw materials, and reacting so as to obtain 4-N-(benzhydryloxycarbonyl) cytosine-acetic acid; and using the 4-N-(benzhydryloxycarbonyl) cytosine-acetic acid as a reactant, and adding the raw materials, thus obtaining the product. The feather weight preparation method is simple in operation and mild in reaction conditions, belongs to the large-scale production technology and provides the material guarantee for the large-scale research of the PNA and the technology guarantee for the subsequent large-scale application.

Description

technical field [0001] The invention relates to the field of medical science and technology, in particular to a kilogram-level preparation method of cytosine-containing PNA monomer. Background technique [0002] Oligonucleotides are widely used in therapeutic drugs, molecular biology research tools and diagnostic reagents. The main constraints of the application of oligonucleotides are that they are easily degraded by nucleases, poor thermal stability after hybridization, and non-specific binding to proteins. In order to modify the physicochemical and biological properties of oligonucleotides, many oligonucleotide analogs have been researched. Peptide nucleic acid is one of the more important oligonucleotide mimics. In 1991, Nielsen et al reported the use of N-(2-aminoethyl)glycine backbone instead of sugar-phosphate backbone as repeating structural unit, and synthesized oligonucleotide mimics linked by peptide bonds, called peptide nucleic acid (Peptide nucleic acid) Nuc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/47
CPCC07D239/47
Inventor 喻国贞吴绍伟刘金永凌静
Owner SUZHOU VIVOTIDE BIOTECH
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