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Synthesis of L-benzyl- glutamic ester polymer

A technology of glutamic acid ester and synthesis method, applied in the chemical industry, can solve the problems of difficult bioactive molecule functionalization of polypeptide, inability to prepare polypeptide-based biological materials, and no preparation method is proposed.

Inactive Publication Date: 2008-12-10
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its shortcomings are: 1. The literature does not propose a preparation method for alkynylated L-benzyl-glutamate polymers with different topological structures, so that it cannot adjust the physical and chemical properties of the polypeptide through macromolecular topological structure control; 2. Since the linear polypeptide has only one terminal amino group, it is difficult to prepare functionalized polypeptides for biologically active molecules; 3. Since it is impossible to prepare polypeptide-based biomaterials with different topological structures, it is not conducive to laboratory and industrial production. application

Method used

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  • Synthesis of L-benzyl- glutamic ester polymer

Examples

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Embodiment 1

[0013] Example 1: Synthesis of Alkynylated L-Benzyl-Glutamate Polymers from Zero-Generation Alkynylated Amide-Amine Polymers

[0014] Pipette propargylamine (PA, 4.1uL, 0.061mmol) into a 25mL well-dried round-bottomed flask Gamma-benzyl-L-glutamic acid-N-carboxy anhydride (BLG-NCA) monomer (800.5 mg, 3.04 mmol) was added into the round bottom flask and dissolved with 8 mL of anhydrous DMF. After the two flasks were evacuated and blown with nitrogen for 3 times, the BLG-NCA was transferred to the flask containing PA with a vacuum line under a nitrogen atmosphere, and then transferred to an oil bath at 25°C for 48 hours. After the reaction was completed, most of the solvent was removed by rotary evaporation under reduced pressure, and the resulting product was dissolved in THF (4 mL), precipitated in anhydrous ether (50 mL), discarded the supernatant, and dried in vacuo to obtain a linear structure with one arm The alkynylated L-benzyl-glutamate polymer (526.6 mg, yield: 79.0%)...

Embodiment 2

[0015] Example 2: Synthesis of Alkynylated L-Benzyl-Glutamate Polymers from a Generation of Alkynylated Amide-Amine Polymers

[0016] Weigh a generation of alkynylated amide-amine polymer (PA-PAMAM-G1, 3.9mg, 0.014mmol) into a 25mL fully dry round-bottomed flask containing magnetons, dissolve with 1mL of anhydrous DMF; in another 25mL Add γ-benzyl-L-glutamic acid-N-carboxy anhydride (BLG-NCA) monomer (734.0mg, 2.79mmol) into a well-dried round bottom flask, and dissolve it with 7mL of anhydrous DMF. Both flasks are evacuated After blowing nitrogen three times, the BLG-NCA was transferred to a flask containing PA-PAMAM-G1 with a vacuum line under a nitrogen atmosphere, and then transferred to a 25oC oil bath to react for 48 hours. After the reaction was complete, most of the solvent was removed by rotary evaporation, and the resulting product was dissolved in THF (4 mL), precipitated in anhydrous ether (50 mL), discarded the supernatant, and dried in vacuo to obtain a fan-shape...

Embodiment 3

[0017] Example 3: Synthesis of Alkynylated L-Benzyl-Glutamate Polymers from Dialkynylated Amide-Amine Polymers

[0018] Weigh the di-alkynylated amide-amine polymer (PA-PAMAM-G2, 102.0mg, 0.14mmol) into a 25mL fully dry round-bottomed flask containing magnetons, dissolve with 1mL of anhydrous DMF; in another Add γ-benzyl-L-glutamic acid-N-carboxy anhydride (BLG-NCA) monomer (727.2mg, 2.76mmol) into a 25mL fully dry round bottom flask, and dissolve it with 7mL of anhydrous DMF. After vacuuming nitrogen for 3 times, the BLG-NCA was transferred to a flask containing PA-PAMAM-G2 with a vacuum line under a nitrogen atmosphere, and then transferred to a 25oC oil bath for 48 hours. After the reaction was completed, most of the solvent was removed by rotary evaporation under reduced pressure, and the resulting product was dissolved in THF (4 mL), precipitated in anhydrous ether (50 mL), discarded the supernatant, and dried in vacuo to obtain a fan-shaped structure with 4 arms. Alkyny...

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Abstract

The invention provides a method for synthesizing a terminal alkynyl L-benzyl-glutaric acid ester polymer with different topological structures. The method is completed by one-step reaction, namely different generations of alkynyl amide-amine polymers are taken as an initiator to initiate ring-opening polymerization of a gamma-benzyl-L-glutamic acid-N-carboxyl anhydride solution so as to prepare the terminal alkynyl L-benzyl-glutaric acid ester polymer with different topological structures; the mol ratio of a gamma-benzyl-L-glutamic acid-N-carboxyl anhydride monomer to primary amino groups in the alkynyl amide-amine polymer initiator is 5 to 100; and the solution polymerization reaction is performed under the condition of 25 DEG C, and the polymerization reaction time is 48 hours. The method provides a simple and effective path for preparing degradable polypeptidyl biomaterials capable of realizing 'clicking' functionalization, and provides a practical and effective path for designing novel degradable biological active materials, control-released drug carriers and so on.

Description

technical field [0001] The invention relates to a method in the technical field of chemical industry, in particular to a method for synthesizing L-benzyl-glutamate polymers with different topological structures through alkynylation. Background technique [0002] Polypeptide or polyamino acid usually refers to a homopolymer or copolymer obtained by polymerization of one or several amino acids, which has a secondary structure similar to that of natural proteins (including α-helix, β-sheet, etc.), and in a certain Under conditions (such as temperature, pH, ionic strength, etc.) the conformation of molecular chains will change each other. At the same time, polyamino acids have good biocompatibility, degradability, self-assembly performance, and adjustable mechanical properties, and have become an important class of biomedical materials. Therefore, the preparation of degradable polypeptides that are easy to functionalize and have different topological structures provides a pract...

Claims

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Application Information

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IPC IPC(8): C08G69/20
Inventor 董常明彭松明华崇
Owner SHANGHAI JIAO TONG UNIV
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