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Peptide-like monomer as well as polymer and application thereof

A technology for polymers and degradable polymers, which is applied in the field of biomedical materials, can solve the problems that the substituent groups cannot be functionally modified, hinder the application of polymer peptide polymers, etc., and achieve rich types, simple and fast synthesis methods, and mild synthesis conditions Effect

Active Publication Date: 2019-06-21
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the current chemically synthesized polymeric peptide polymers are limited to side groups that are non-reactive alkyl groups. These substituent groups cannot be functionally modified, which seriously hinders the application of polymeric peptide polymers.

Method used

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  • Peptide-like monomer as well as polymer and application thereof
  • Peptide-like monomer as well as polymer and application thereof
  • Peptide-like monomer as well as polymer and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0050] Embodiment 1: the preparation of azidoalkyl alcohol compound

[0051] Bromopropanol (1.38g, 0.01mol) and sodium azide (0.975g, 0.015mol) were weighed and dissolved in N,N-dimethylformamide (DMF), and reacted at 90°C for 12h under nitrogen protection. After the reaction, the solution was cooled to room temperature, diluted with a certain amount of water, and the aqueous layer was washed with a large amount of ether to extract the product, the ether solution was collected and washed with anhydrous NaSO 4 Dry overnight, filter and concentrate the crude product to remove residual DMF organic solvent by column chromatography, developing agent is ethyl acetate:petroleum ether=1:5, the colorless liquid obtained is the product azidopropanol, yield It was 0.873g, and the yield was 86.4%. Using the same procedure, azidohexanol (0.69 g, 89.2%) and azidedecanol (0.98 g, 91.7%) can be prepared.

[0052]

[0053] Azidopropanol (m=1) 1 H NMR (CDCl 3 ):δ=3.74(-CH 2 N 3 ),3.4...

Embodiment 2

[0057] Embodiment 2: Preparation of N-hydroxyalkyl-β-alanine carboxylic acid anhydride compound

[0058] Dissolve azidopropanol and succinic anhydride in hexafluoroisopropanol (HFIP) at a molar ratio of 1.2:1, slowly add 1.1 equivalents of boron trifluoride ether as a catalyst, and react the reaction solution in a glove box for 6 hours at low temperature. There will be more N in the early stage of the reaction 2 Therefore, it is necessary to continuously rotate the piston to remove the gas in the system. After the reaction, anhydrous pyridine equivalent to boron trifluoride ether was slowly added dropwise to the reaction liquid to neutralize the acid in the system, and the stirring was continued for 1 h. After the reaction solution is concentrated, it is purified and separated by column chromatography in the glove box. The ratio of developing agent ethyl acetate / petroleum ether is 1:2, and the collected solution is concentrated to prepare N-hydroxypropyl-β-alanine carboxyli...

Embodiment 3

[0068] Example 3: Preparation of Polypeptide Poly(N-hydroxyundecyl-β-alanine) (PC11OHNNCA)

[0069] Dissolve a certain amount of monomer N-hydroxyl undecyl-β-alanine carboxylic anhydride in a certain amount of dry DMF solvent in the glove box, then add benzylamine initiator in the system (initiator dose is determined according to the theoretical design molecular weight , such as the design degree of polymerization is 50, the amount of benzylamine is 1 / 50 of the molar amount of the monomer), and placed in an oil bath at 50° C. under the protection of argon for sealing reaction for 24 hours. After the reaction, the reaction solution was returned to room temperature, and was repeatedly settled three times in a large amount of anhydrous ether, and then dried in vacuum to obtain the polymer product. The synthesis methods of other types of clustered peptides are similar to the above operations.

[0070]

[0071] Poly(N-hydroxyundecyl-β-alanine) (PC11OHNNCA) NMR: 1 H NMR (CDCl...

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Abstract

The invention provides a peptide-like monomer as well as a polymer and an application thereof. The structural formula of the peptide-like monomer is shown in a formula I, wherein n is any integer of 1to 6; R is H, C1-C12 non-reactive alkyl or C1-C12 reactive alkyl, the C1-C12 non-reactive alkyl is linear or branched chain alkyl without active groups, the C1-C12 reactive alkyl is linear or branched chain alkyl containing active groups, and the active groups comprise at least one of hydroxyl, alkenyl, alkynyl, halogen and mercapto; the cyclic structure of the peptide-like monomer is oxygen-containing anhydride or sulfur-containing thioanhydride. The invention further provides a preparation method of the polymer of the peptide-like monomer and a preparation method of a modified polymer. Various clustering peptide polymers can be directly prepared from the peptide-like monomer through ring-opening polymerization, and the prepared functionalized clustering peptide polymer can be subjectedto various functional modification and is applied to the field of biomedical materials.

Description

technical field [0001] The present invention relates to the field of biomedical materials, in particular, to a peptide-like monomer and its polymer and its application; more specifically, to a biodegradable medical polymer material, a peptide-like monomer and its polymer, and a preparation method and apply. Background technique [0002] Clustering peptides are biodegradable polymers constructed with N-substituted glycine or alanine as repeating units. As a derivative of a polypeptide, its side group replaces the hydrogen on the amide bond of the polypeptide main chain, eliminating the hydrogen bond donor, so there is no inherent intramolecular or intermolecular hydrogen in the polymer main chain of the polymeric peptide The properties of bond interactions and chiral centers are mainly determined by the types of side group substituents and their physical and chemical properties. Such a structure makes the polymeric peptide polymers have better flexibility, and have good sol...

Claims

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Application Information

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IPC IPC(8): C07D265/06C08G69/14C08G69/16C08G69/42
Inventor 朱新远张俊范文彬张川薛锋童刚生
Owner SHANGHAI JIAO TONG UNIV