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Feather weight PNA (pentose nucleic acid) synthesis method

A kilogram-scale, 6-N- technology, applied in the field of synthetic PNA, can solve problems such as restricting PNA application research work and small synthesis scale.

Inactive Publication Date: 2013-06-12
SUZHOU VIVOTIDE BIOTECH
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  • Abstract
  • Description
  • Claims
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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.

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  • Feather weight PNA (pentose nucleic acid) synthesis method

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Embodiment Construction

[0023] The present invention will be described in detail below in conjunction with embodiments.

[0024] A method for synthesizing PNA at a kilogram level, comprising the following steps:

[0025] 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%;

[0026] 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 ...

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Abstract

The invention discloses a feather weight PNA (pentose nucleic acid) synthesis method. The method comprises the following steps: reacting ethylene diamine with chloroacetic acid, and recrystallizing with DMSO to obtain N-(2-aminoethyl)glycine; by taking the N-(2-aminoethyl)glycine as a reactant, adding raw materials, and reacting to obtain N-(2-Fmoc-aminoethyl)glycine methyl ester hydrochloride; by taking adenine as a reactant, adding raw materials, and reacting to obtain 9-ehtyl acetate adenine; by taking the 9-ehtyl acetate adenine and carbonyl diimidazole as reactants, adding raw materials, and reacting to obtain 6-N-(benzhydryloxycarbonyl)adenine-9-acetic acid; by taking the 6-N-(benzhydryloxycarbonyl)adenine-9-acetic acid as a reactant, adding raw materials, and reacting to obtain the PNA. The feather weight PNA synthesis method belongs to large-scale production technology, does material preparation for the large-scale research of the PNA, as well as technological preparation for the future large-scale application.

Description

technical field [0001] The invention relates to a method for synthesizing PNA, in particular to a method for synthesizing PNA at a kilogram level. 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 connected by peptide bonds, called peptide nucleic acid (Peptide nucleic acid) acid, PNA). Although the structu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/34
Inventor 凌静刘金永
Owner SUZHOU VIVOTIDE BIOTECH
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