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One-pot method for preparing functionalized polypeptides

A functionalized, polypeptide technology, applied in the preparation methods of peptides, chemical instruments and methods, peptides, etc., can solve the problems of the inability to achieve the molecular weight of the polypeptide, the controllability of the polymerization reaction, and the binding of the polypeptide, etc. Controllable topology, high catalytic activity, and cheap and easy-to-obtain reaction raw materials

Active Publication Date: 2021-04-30
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 also be isomerized into isocyanate anion to terminate the polymerization reaction, which will greatly reduce the controllability of the polymerization reaction. 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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  • One-pot method for preparing functionalized polypeptides
  • One-pot method for preparing functionalized polypeptides
  • One-pot method for preparing functionalized polypeptides

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 acid anhydride monolayer in the amino acid ring. The results showed that the conversion rate of the monomer was 99%; the molecular weight Mn of the functionalized peptide was 10,900 ...

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 acid anhydride monolayer in the amino acid ring. The results showed that the monomer conversion rate was 99%; the molecular weight Mn of the functionalized peptide was 10,900 and the molecular we...

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Abstract

A one-pot method for preparing functionalized polypeptides. At room temperature, acrylate functional small molecules and secondary amine amino alcohols are dissolved in organic solvents to react to generate functional tertiary amine amino alcohol initiators. The catalyst thiourea and the acid anhydride monomer in the amino acid ring are sequentially added to trigger the ring-opening polymerization of the NCA monomer to generate a functionalized polypeptide at the end of the chain or at the center of the chain. The experimental route of the present invention is simple and clear, the raw materials are cheap and easy to obtain, and the reaction conditions are mild. It has the characteristics of clean, no metal residue, molecular weight and molecular weight distribution controllable.

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 Patents(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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