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Synthesis and application of ε-(1-o-nitrophenyl)ethoxycarbon-l-lysine-n-carboxylic acid anhydride

A technology of o-nitrophenyl and nitrophenyl, applied in organic chemistry and other fields, can solve the problems of low molecular weight of polymers, side reactions of imidization, slow photopolymerization rate, etc.

Active Publication Date: 2019-12-10
SHANGHAI JIAO TONG UNIV
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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

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  • Synthesis and application of ε-(1-o-nitrophenyl)ethoxycarbon-l-lysine-n-carboxylic acid anhydride
  • Synthesis and application of ε-(1-o-nitrophenyl)ethoxycarbon-l-lysine-n-carboxylic acid anhydride
  • Synthesis and application of ε-(1-o-nitrophenyl)ethoxycarbon-l-lysine-n-carboxylic acid anhydride

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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...

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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

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/44C08G83/00
CPCC07D263/44C08G83/005
Inventor 李攀董常明
Owner SHANGHAI JIAO TONG UNIV
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