Unlock instant, AI-driven research and patent intelligence for your innovation.

Synthesis and application of epsilon-(1-o-nitrophenyl) ethoxycarbonyl-L-lysine-N-carboxy anhydride

A technology of o-nitrophenyl and nitrophenyl, which is applied in the field of light-controlled polymerization and hyperbranched peptides, can solve the problems of low polymer molecular weight, side reactions of imidization, and slow light-controlled polymerization rate, etc.

Active Publication Date: 2018-07-24
SHANGHAI JIAO TONG UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this system, the o-nitrosobenzaldehyde produced by photolysis and the terminal amine group of the lysine unit in the polymer will have a serious imidization side reaction, and the photopolymerization rate is slow, and the prepared polymer Relatively low molecular weight

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis and application of epsilon-(1-o-nitrophenyl) ethoxycarbonyl-L-lysine-N-carboxy anhydride
  • Synthesis and application of epsilon-(1-o-nitrophenyl) ethoxycarbonyl-L-lysine-N-carboxy anhydride
  • Synthesis and application of epsilon-(1-o-nitrophenyl) ethoxycarbonyl-L-lysine-N-carboxy anhydride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Step 1, 1.34g (8mmol) 1-(2-nitrophenyl) ethanol, 488mg (4mmol) 4-dimethylaminopyridine, 1.12mL (8mmol) triethylamine was dissolved in 25mL anhydrous dichloromethane, 2.42 g (12 mmol) of phenyl p-nitrochloroformate was dissolved in 15 mL of anhydrous dichloromethane and slowly added dropwise to the above solution, and reacted at 30°C for 8 hours. The reaction solution was washed successively with 1N dilute hydrochloric acid and saturated aqueous sodium bicarbonate solution, and the organic phase was dried overnight with anhydrous magnesium sulfate and then concentrated. The crude product was purified by column chromatography (ethyl acetate / petroleum ether=1 / 5) to obtain a nearly colorless Viscous liquid (NPE-NPC). The whole process of the above operation was protected from light, the yield: 2.53g (7.61mmol), and the yield was 95.6%.

[0053] Step 2, 2.96g (12mmol) N-(tert-butoxycarbonyl)-L-lysine, 1.02g (12mmol) sodium bicarbonate dissolved in 20mL deionized water, 2.66...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
molecular weightaaaaaaaaaa
Branching factoraaaaaaaaaa
Login to View More

Abstract

The invention relates to synthesis and application of epsilon-(1-O-nitrophenyl) carbethoxy-L-lysine-N-carboxy anhydride. A photo-sensitive monomer NPE-Lys NCA is synthesized through four-step chemicalreaction; hyper-branched polypeptides are directly prepared through UV irradiation, namely the NPE-Lys NCA monomer is synthesized by coupling 1-(2-nitrophenyl) ethanol and N-(tertiary oxo carbonyl)-L-lysine through a carbamate bond, then removing t-butyloxycarboryl, converting into hydrochloride and further adopting a three-phosgene ring closing; finally, the hyper-branched polypeptide is prepared by blowing nitrogen into a polymerization solution by adopting a needle head, irradiating an acetone solution of the monomer through different intensities of ultraviolet light and adopting a one-potmethod. Under the condition of no additional catalyst or initiator, the one-pot photo-polymerization and the rapid preparation of the hyper-branched polypeptide with different branching degrees and different molecular weights are realized, and an experiment platform is provided for further construction of a targeted and stimulus-responsive polymer nano-drug carrier.

Description

technical field [0001] The invention belongs to the technical field of chemical engineering, and in particular relates to the synthesis of photocleavable amino acid monomer ε-(1-o-nitrophenyl)ethoxycarbonyl-L-lysine-N-carboxylic acid anhydride (NPE-Lys NCA) and Its one-pot photopolymerization of hyperbranched polypeptides under ultraviolet light irradiation. Background technique [0002] At present, the synthesis methods of hyperbranched peptides mainly focus on AB 2 The thermal polycondensation of amino acid monomers and the iterative ring-opening polymerization of amino acid-N-carboxylic acid anhydride monomers (NCA), the main disadvantage of the former is that there are few types of monomers to choose from, and it is not easy to adjust the molecular weight and branching of polymers. degree; and the synthesis and purification steps of the latter are too complicated. The above shortcomings restrict the precise preparation, performance regulation and wide application of hy...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/44C08G83/00
CPCC07D263/44C08G83/005
Inventor 李攀董常明
Owner SHANGHAI JIAO TONG UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com