Dendrimer with alkynyl core and outer amino acid shell, and Huisgen 1,3-dipolar cycloaddition synthetic method and application thereof

A technology of dendrimers and amino acids, applied in chemical instruments and methods, other chemical processes, organic chemistry, etc., can solve problems such as structural defects of dendrimers, difficulty in dendrimer purification, easy side reactions, etc.

Active Publication Date: 2012-10-17
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This not only wastes the reaction raw materials, but also the excess reaction raw materials are not easy to clean up, and it is easy to produce side reactions, which brings difficulties to the purification of dendrimers
In addition, when functional ligands are connected to the outer layer of PAMAM, the synthesized dendrimers with functional ligands in the outer layer may have structural defects due to the existence of steric hindrance.

Method used

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  • Dendrimer with alkynyl core and outer amino acid shell, and Huisgen 1,3-dipolar cycloaddition synthetic method and application thereof
  • Dendrimer with alkynyl core and outer amino acid shell, and Huisgen 1,3-dipolar cycloaddition synthetic method and application thereof
  • Dendrimer with alkynyl core and outer amino acid shell, and Huisgen 1,3-dipolar cycloaddition synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Embodiment 1: Synthetic method of dendrimers whose inner core is alkynyl and outer layer is phenylalanine

[0094] (1) Synthesis of dendrimers whose outer layer is azide group

[0095] (a) Synthesis of 1,3-diazido-2-propanol (C-1)

[0096] Dissolve 2.356g (36.2mmol) sodium azide in 15.0ml H 2 O, 1.340g (14.5mmol) epichlorohydrin dissolved in 15.0ml acetonitrile; mix the two, react at 85±3°C for 36 hours, remove the acetonitrile in the reaction system by rotary evaporation; extract once with 50ml ethyl acetate , and then extracted three times with 25ml of water; the extracted oil phase was extracted with anhydrous MgSO 4 After drying, suction filtration and distillation yielded 1.466 g of compound 1,3-diazido-2-propanol (C-1). (b) Generation 0.5 dendrimers with an azide-based outer layer (G0.5-N 3 )Synthesis

[0097] Dissolve 1.552g (7.7mmol) p-nitrophenyl chloroformate and 0.998g (7.0mmol) 1,3-diazido-2-propanol in 5.0ml dichloromethane and 7.0ml dichloromethane, r...

Embodiment 2

[0134] Example 2: Synthesis of a dendrimer whose inner core is an alkyne group and whose outer layer is L-histidine

[0135] (1) Synthesis of dendrimers whose outer layer is azide group

[0136] (a) Synthesis of 1,3-diazido-2-propanol (C-1)

[0137] Dissolve 1.177g (18.1mmol) sodium azide in 15.0ml H 2 In O, 0.837g (9.0mmol) of epichlorohydrin was dissolved in 15.0ml of acetonitrile; the two were mixed and reacted at 95°C for 48 hours; the acetonitrile in the reaction system was removed by rotary evaporation; then, extracted with 60ml of ethyl acetate once, then extracted three times with 25ml water; the oil phase after extraction was extracted with anhydrous MgSO 4 After drying, suction filtration and rotary evaporation, 0.611 g of 1,3-diazido-2-propanol was obtained.

[0138] (b) Generation 0.5 dendrimers with an azide-based outer layer (G0.5-N 3 )Synthesis

[0139] Dissolve 2.821g (14.0mmol) p-nitrophenyl chloroformate and 0.994g (7.0mmol) 1,3-diazido-2-propanol in 5.0...

Embodiment 3

[0159] Example 3: Synthesis of dendrimers whose inner core is alkynyl and outer layer is tryptophan

[0160] (1) Synthesis of dendrimers whose outer layer is azide group

[0161] (a) Synthesis of 1,3-diazido-2-propanol (C-1)

[0162] Dissolve 3.059g (47.1mmol) sodium azide in 15.0ml H 2 In O, 1.455g (15.7mmol) of epichlorohydrin was dissolved in 15.0ml of acetonitrile; the two were mixed and reacted at 95°C for 24 hours; the acetonitrile in the reaction solution was removed by rotary evaporation; then, 60ml of ethyl acetate was used to Extract once, and then extract three times with 25ml of water. The extracted oil phase was anhydrous MgSO 4 After drying, suction filtration and vacuum distillation, 1.576 g of compound 1,3-diazido-2-propanol was obtained.

[0163] (b) Generation 0.5 dendrimers with an azide-based outer layer (G0.5-N 3 )Synthesis

[0164] Dissolve 1.919g (9.5mmol) of p-nitrophenyl chloroformate and 1.352g (9.5mmol) of 1,3-diazido-2-propanol (C-1) in 5.0ml ...

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Abstract

The invention discloses a dendrimer with an alkynyl core and an outer amino acid shell, and a Huisgen 1,3-dipolar cycloaddition synthetic method and application thereof. In the preparation process of the dendrimer, 0.5-G, 1.5-G, 2.5-G or 3.5-G dendrimer molecules with an outer azido shell are synthesized; the dendrimer molecules and ascorbic acid/copper sulfate composing a catalytic system are added into alkynylated tertbutyloxycarbonyl-amino acid dissolved in DMF, so that the dendrimer molecules with the outer azido shell and ethynylated amino acids are bonded together through Huisgen 1,3-dipolar cycloaddition; after a reaction at a temperature of 15 to 35 DEG C for 4 to 24 hours, dichloromethane is added to dilute a reaction solution, and then extraction with water is carried out. The invention has the following advantages: reaction specificity is good, reaction efficiency is high, and the outer shell of the dendrimer has a plurality of amino acid ligands, which enables a prepared adsorption material to have better protein separation or blood purification effects compared with common adsorption materials with a space arm as a single active site.

Description

technical field [0001] The invention relates to the application of Huisgen 1,3-dipolar cycloaddition reaction in the synthesis of dendrimers, in particular to a dendrimer whose inner core is alkynyl and outer layer is amino acid and a preparation method thereof. technical background [0002] Dendrimers are highly branched macromolecules obtained by stepwise reactions of multifunctional monomers. Its structure mainly includes three parts, which are the core that triggers the reaction, the outer layer at the outermost end of the dendrimer, and the inner arm between the inner core and the outer layer. Its structure has a high degree of symmetry and regularity, and the shape of the molecule and the number of functional groups on the outer layer can be precisely controlled; compared with traditional polymers, the molecular weight distribution of dendrimers is monodisperse. [0003] PAMAM is a very common dendritic macromolecule at present. Its synthetic basic reaction mainly inc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/04C07D403/12B01J20/26B01J20/30
Inventor 李光吉黄恩德
Owner SOUTH CHINA UNIV OF TECH
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