Feather weight synthesis method of Fmoc-PNA-T-OH

A fmoc-pna-t-oh, kilogram-level technology, applied in the field of PNA synthesis, 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

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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

Method used

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  • Feather weight synthesis method of Fmoc-PNA-T-OH
  • Feather weight synthesis method of Fmoc-PNA-T-OH
  • Feather weight synthesis method of Fmoc-PNA-T-OH

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Embodiment Construction

[0020] The present invention will be described in detail below in conjunction with the embodiments.

[0021] A kilogram-level synthesis of Fmoc-PNA-T-OH method includes the following steps:

[0022] Step 1) 1 liter three-necked flask is filled with 500 ml of ethylene diamine, cooled to 10 degrees in an ice bath, and 75 g of chloroacetic acid is added in batches to control the temperature below 10 degrees. After each batch is added, observe that it is completely consumed before adding One batch, after the addition is complete, react overnight at room temperature, spin-dry the ethylenediamine, recover the ethylenediamine for recycling, use an oil pump to remove the ethylenediamine as much as possible, and recrystallize with DMSO to obtain white powdery crystals, which are N- (2-Aminoethyl)glycine, the yield is 40-50%;

[0023] Step 2) Dissolve 50g of N-(2-aminoethyl)glycine in a mixed solution of 850ml of dichloromethane and 50ml of N,N-dimethylformamide, add 134ml of trimethylchloros...

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Abstract

The invention discloses a feather weight synthesis method of Fmoc-PNA-T-OH. The feather weight synthesis method comprises the following steps: reacting ethanediamine serving as a raw material with haloacetic acid, and recrystallizing by using DMSO (dimethylsulfoxide) so as to obtain N-(2-aminoethyl) glycine; reacting the N-(2-aminoethyl) glycine serving as a raw material with Fmoc-osu so as to obtain N-(2-Fmoc-aminoethyl) glycine, and then reacting with methyl alcohol so as to obtain N-(2-Fmoc-aminoethyl) glycine methyl ester hydrochloride; using thymine as a raw material, adding raw materials, and reacting so as to obtain 1-carbethoxy thymine; reacting the 1-carbethoxy thymine serving as the raw material with the N-(2-Fmoc-aminoethyl) glycine methyl ester so as to obtain Fmoc-PNA-T-OMe; and hydrolyzing the Fmoc-PNA-T-OMe so as to obtain the product.

Description

Technical field [0001] The invention relates to a method for synthesizing PNA, in particular to a method for synthesizing Fmoc-PNA-T-OH at 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, have poor thermal stability after hybridization, and non-specifically bind to proteins. In order to modify the physical, chemical and biological properties of oligonucleotides, many oligonucleotide analogs have been studied. 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 the repeating structural unit to synthesize an oligonucleotide mimic linked by peptide bonds, called peptide nucleic acid (Peptide Nucleic Acid). nucleic acid, PNA). Alt...

Claims

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Application Information

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IPC IPC(8): C07D239/54
CPCC07D239/54
Inventor 凌静杜建坤刘金永黄忠林
Owner SUZHOU VIVOTIDE BIOTECH
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