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Synthesis method of related polypeptide

A synthetic method and type of technology, applied in the field of peptide-like synthesis, can solve the problems of limitations, harshness, and unsuitability for large-scale synthesis, and achieve the effect of facilitating polymerization and increasing the reaction rate

Inactive Publication Date: 2015-12-30
NANJING UNIV OF TECH
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AI Technical Summary

Problems solved by technology

However, nitrogen heterocyclic carbene is extremely active, sensitive to air and water, and has a lifespan of only a few seconds in air. Directly catalyzing ring-opening polymerization requires very harsh conditions, so this method is not suitable for large-scale synthesis
Subsequently, Luxenhofer et al. published "Polypeptoids from N-Substituted Glycine N-Carboxyanhydrides: Hydrophilic, Hydrophobic, and Amphiphilic Polymers with Poisson Distribution" (from N-substituted glycine-N-carboxy anhydride polypeptides: hydrophobic, hydrophilic water, amphiphilic copolymer), the paper reported that under vacuum conditions, benzylamine was used to initiate ring-opening polymerization of N-substituted glycine-N-carboxy anhydrides to prepare peptide-like peptides, but high vacuum conditions are not suitable for industrial production, so this method has also been obtained. limit

Method used

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Experimental program
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Effect test

Embodiment 1

[0035] Such as figure 1 As indicated, under the condition of nitrogen flow, N-methyl substituted glycine-N-carboxy anhydride (0.2581g, 2.3mmol) was dissolved in 2.3mL of anhydrous acetonitrile, after complete dissolution, benzylamine (10uL, 0.092mmol) added to the solution ([monomer] 0 / [initiator 0 ]=25). The reaction solution was reacted at room temperature under nitrogen flow. After reacting for 4 hours, the reaction liquid was added into excess diethyl ether to precipitate a polymer, and then the polymer was vacuum-dried. polymer structure through 1 HNMR with 13 CNMR identification (see figure 2 and image 3 ), the molecular weight and degree of dispersion of the polymer are measured by GPC (gel permeation chromatography). GPC test conditions: flow rate 1mL / min, mobile phase DMF, temperature 50°C. From Figure 4 In the reaction kinetic curve, we found that the reaction rate was significantly increased under the action of nitrogen flow. (number average molecular...

Embodiment 2

[0037] Under the condition of nitrogen flow, N-methyl-substituted glycine-N-carboxy anhydride (3.097g, 27.6mmol) was dissolved in 27.6mL of anhydrous dichloromethane, after complete dissolution, propylamine (7.5uL, 0.092 mmol) was added to the solution ([monomer] 0 / [initiator 0 ]=300). The reaction solution was reacted at room temperature under nitrogen flow. After reacting for 4 hours, the reaction liquid was added into excess diethyl ether to precipitate a polymer, and then the polymer was vacuum-dried. polymer structure through 1 HNMR with 13 CNMR identification, molecular weight and dispersion of the polymer are measured by GPC (gel permeation chromatography). GPC test conditions: flow rate 1mL / min, mobile phase DMF, temperature 50°C. (number average molecular weight 20.7 kg / mol; molecular weight distribution 1.08; yield 92.1%).

Embodiment 3

[0039] Under nitrogen flow conditions, N-ethyl substituted glycine-N-carboxy anhydride (1.1860g, 9.2mmol) was dissolved in 9.2mL of anhydrous acetonitrile, after complete dissolution, benzylamine (10uL, 0.092mmol) added to the solution ([monomer] 0 / [initiator 0 ]=100). The reaction solution was reacted at room temperature under nitrogen flow. After reacting for 8 hours, the reaction liquid was added into excess diethyl ether to precipitate the polymer, and then the polymer was vacuum-dried. polymer structure through 1 HNMR with 13 CNMR identification, molecular weight and dispersion of the polymer are measured by GPC (gel permeation chromatography). GPC test conditions: flow rate 1mL / min, mobile phase DMF, temperature 50°C. (number average molecular weight 1.8 kg / mol; molecular weight distribution 1.22; yield 86.1%).

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Abstract

The invention discloses a synthesis method of related polypeptide, and belongs to the technical field of high polymer materials. With alkyl primary amine or aromatic amine as an initiator and N-substituted glycine-N-carboxy anhydrides as a monomer, solution ring opening polymerization of the N-substituted glycine-N-carboxy anhydrides is initialized under the condition of nitrogen flow to prepare the related polypeptide. Carbon dioxide generated in the reaction process is rapidly discharged in a manner of nitrogen flow, so that the reaction rate is improved; the polymerization reaction is facilitated; and the related polypeptide generated by the polymerization according to the method is relatively narrow in molecular weight distribution.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to a synthetic method of a quasi-polypeptide. Background technique [0002] Peptide-like peptides are a class of biomimetic peptides. In recent years, they have received extensive attention and research in the fields of drug-controlled release systems, smart coatings, and bio-nanotechnology. [0003] There have been some studies on the synthesis of peptide-like peptides. For example, early researchers used a step-by-step synthesis method to prepare peptide-like peptides. However, the synthesis of peptide-like by this method has some limitations such as: time-consuming, low yield, low degree of polymerization, etc., so this method is not suitable for peptide-like with high degree of polymerization. Later, Zhang et al published "CyclicPoly(α-peptoid)sandTheirBlockCopolymersfromN-HeterocyclicCarbene-MediatedRing-OpeningPolymerizationsofN-SubstitutedN-Carboxylanhy...

Claims

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Application Information

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IPC IPC(8): C08G69/00
Inventor 郭凯崔赛德李振江王鑫潘先福王慧颖智绪
Owner NANJING UNIV OF TECH
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