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Method of preparing functional polypeptide by one-pot method

A functional peptide technology, applied in the preparation method of peptides, chemical instruments and methods, peptides, etc., can solve the problems of inability to realize the molecular weight of peptides, reduce the controllability of polymerization reactions, bind peptides, etc., and achieve a simple and clear reaction route. High catalytic activity, cheap and easy-to-obtain reaction raw materials

Active Publication Date: 2019-04-09
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reactions in the above two mechanisms are the side reactions of each other. At the same time, the NCA anion will be isomerized into isocyanate anion to terminate the polymerization reaction, which greatly reduces the controllability of the polymerization reaction, and cannot realize the microstructure of the polypeptide including molecular weight, molecular weight distribution, Molecular topology, especially the precise regulation of chain end groups, has become a bottleneck for the widespread application of tethered peptides

Method used

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  • Method of preparing functional polypeptide by one-pot method
  • Method of preparing functional polypeptide by one-pot method
  • Method of preparing functional polypeptide by one-pot method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] At room temperature, add 37.99 μmol of acrylate functional small molecules, 37.99 μmol of secondary amine-type amino alcohol and 10 ml of organic solvent methylene chloride into a 25 ml polymerization bottle that has undergone anhydrous treatment, react at 25°C for 10 minutes, and then add 37.99μmol of thiourea catalyst, after stirring for 5min, add 1.90mmol of amino acid anhydride monomer into the polymerization bottle, and then after 0.2h of polymerization reaction at 25°C, add ethanol with a volume fraction of 10% hydrochloric acid into the polymerization bottle The solution terminated the reaction, the reaction solution was poured into ethanol to settle, filtered to obtain a white solid, the solid was placed in a drying oven, and dried at 40°C for 48 hours to obtain a solid with a net weight of 0.41g. The amino acid ring was detected by infrared testing. The conversion rate of the acid anhydride monomer, the result shows that the conversion rate of the monomer is 99%...

Embodiment 2

[0040] At room temperature, add 37.99 μmol of acrylate functional small molecules, 37.99 μmol of secondary amine-type amino alcohol and 10 ml of organic solvent THF to 25 ml of anhydrous-treated polymerization bottle, react at 25 °C for 10 minutes, and then add 37.99 μmol of Thiourea catalyst, after stirring for 5min, add 1.90mmol amino acid anhydride monomer in the polymerization bottle, then after 0.2h of polymerization at 25°C, add ethanol solution of hydrochloric acid with a volume fraction of 10% to the polymerization bottle to terminate reaction, the reaction solution was poured into ethanol to settle, filtered to obtain a white solid, the solid was placed in a drying oven, and dried at 40°C for 48 hours to obtain a solid with a net weight of 0.41g, and an infrared test was used to detect the amino acid anhydride single The results showed that the conversion rate of the monomer was 99%; the molecular weight Mn of the functionalized peptide was 10,900 and the molecular wei...

Embodiment 3

[0042]At room temperature, add 37.99 μmol of acrylate functional small molecules, 37.99 μmol of secondary amine-type amino alcohol and 10 ml of organic solvent DMF into a 25 ml polymerization bottle that has undergone anhydrous treatment, and then add 37.99 μmol Thiourea catalyst, after stirring for 5min, add 1.90mmol amino acid anhydride monomer in the polymerization bottle, then after 0.2h of polymerization at 25°C, add ethanol solution of hydrochloric acid with a volume fraction of 10% to the polymerization bottle to terminate reaction, the reaction solution was poured into ethanol to settle, filtered to obtain a white solid, the solid was placed in a drying oven, and dried at 40°C for 48 hours to obtain a solid with a net weight of 0.41g, and an infrared test was used to detect the amino acid anhydride single The results showed that the monomer conversion rate was 99%; the molecular weight Mn of the functionalized peptide was 10,900 and the molecular weight distribution was...

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Abstract

The invention relates to a method of preparing functional polypeptide by a one-pot method. The method comprises the following steps: dissolving acrylate functional small molecules and secondary amineamino alcohol in an organic solvent at constant temperature to react to generate a functional tertiary amine amino alcohol initiator; and then successively adding a catalyst thiourea, an amino acid intra-annular anhydride monomer to initiate ring opening polymerization of an NCA monomer to generate a chain end or chain center functional polypeptide. The method is simple and clear in experimental route, low in price and easily available in raw material and mild in reaction condition, and the obtained functional polypeptide has the characteristics of being clear, free of metal residues and controllable in molecular weight and molecular distribution.

Description

technical field [0001] The invention belongs to the technical field of polymer material synthesis, and in particular relates to a method for preparing functionalized polypeptides in one pot. Background technique [0002] Polymers with specific functional groups at their end groups are of great significance in both scientific research and practical applications. The potential applications of polymers can be investigated in a wide range by exploiting the reactivity of polymer terminal functional groups. In the field of polymer synthesis, this polymer can be used as a macromolecular initiator to prepare polymers with structures such as star-shaped hybrid arms, sparse types, grafts, rings, blocks, and networks. offers the possibility. In practical industrial applications, polymer chains can form special aggregated forms (in solution) or microphase structures (in bulk) by utilizing special interactions between specific functional groups, such as hydrogen bonding, charge effects...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/10C07K14/00C07K1/02
CPCC07K14/00C08G69/10
Inventor 赵伟吕岩凤冯子昊梁振华段超倪永浩
Owner SHAANXI UNIV OF SCI & TECH
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