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Synthetic method of saccharide-containing copolymer with biological specific recognition performance

A synthesis method and copolymer technology, which is applied in the measurement of color/spectral characteristics, etc., can solve the problems of difficult synthesis of dendritic sugar-containing polymers, and achieve the effects of reliable polymer synthesis methods, broadening the scope of practical applications, and clear structures

Inactive Publication Date: 2019-09-27
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, most of the sugar-containing polymers obtained by the ROMP polymerization of sugar-containing monomers without protective groups are linear polymers. Although the dendritic sugar-containing polymers can significantly improve the "sugar cluster effect", however, the current dendritic sugar-containing polymers more difficult to synthesize

Method used

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  • Synthetic method of saccharide-containing copolymer with biological specific recognition performance
  • Synthetic method of saccharide-containing copolymer with biological specific recognition performance
  • Synthetic method of saccharide-containing copolymer with biological specific recognition performance

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] In this example, alkyne-terminated norbornene derivatives and azide-containing sugar compounds were used as raw materials to synthesize and prepare by copper-catalyzed azide-terminal alkyne [3+2] cycloaddition (CuAAC) reaction. NB-2Man-OAc and NB-2Gal-OAc two types of sugar-containing polymer monomers with protective groups, followed by ring-opening metathesis polymerization (ROMP) to prepare block copolymers P((( NB-2Man-OH)-b-(NB-2Gal-OH)).

[0055] 1. Synthesis of norbornene dicarboxamide propylene glycol NB-2OH (2)

[0056] Take the three-neck round bottom bottle cooled after high temperature treatment, add cis-5-norbornene-exo-2,3-dicarboxylic acid anhydride (1g, 6.1mmol) and aminomethylpropanediol (0.96g, 9.15mmol), and add 30mL of toluene. Connect the h-type water separator at the mouth of the bottle, connect the serpentine condenser above it, and reflux the reaction in an oil bath at 135°C for 16 hours. After the reaction, the toluene is distilled off under re...

Embodiment 2

[0072] In this example, alkyne-terminated norbornene derivatives and azide-containing sugar compounds were used as raw materials to synthesize and prepare by copper-catalyzed azide-terminal alkyne [3+2] cycloaddition (CuAAC) reaction. NB-2Man-OAc and NB-2Gal-OAc two types of sugar-containing polymer monomers with protective groups, followed by ring-opening metathesis polymerization (ROMP) to prepare block copolymers P((( NB-2Man-OH)-b-(NB-2Gal-OH)).

[0073] 1. Synthesis of norbornene dicarboxamide propylene glycol NB-2OH (2)

[0074] Take the three-neck round bottom bottle cooled after high temperature treatment, add cis-5-norbornene-exo-2,3-dicarboxylic acid anhydride (1g, 6.1mmol) and aminomethylpropanediol (0.96g, 9.15mmol), and add 30mL of toluene. Connect the h-type water separator at the mouth of the bottle, connect the serpentine condenser above it, and reflux the reaction in an oil bath at 135°C for 16 hours. After the reaction, the toluene is distilled off under re...

Embodiment 3

[0086] In this example, alkyne-terminated norbornene derivatives and azide-containing sugar compounds were used as raw materials to synthesize and prepare by copper-catalyzed azide-terminal alkyne [3+2] cycloaddition (CuAAC) reaction. NB-2Man-OAc and NB-2Gal-OAc two types of sugar-containing polymer monomers with protective groups, followed by ring-opening metathesis polymerization (ROMP) to prepare block copolymers P((( NB-2Man-OH)-b-(NB-2Gal-OH)).

[0087] Step 1 and Step 2 are the same as in Example 1.

[0088] 3. Synthesis of NB-2Man-OAc (M1) containing bilateral α-D-mannose norbornene derivative monomer

[0089]Add 2,2-diyne-norbornenedicarboxamide diethyl ether (1.465 g, 4.5 mmol) and acetyl-protected α-D-mannose azide (1.4 g, 3.75 mmol) into a dry reaction flask ), and tert-butanol (8 mL) and deionized water (4 mL) were added. Then copper sulfate pentahydrate (0.5625g, 2.25mmol) and sodium ascorbate (0.74g, 3.75mmol) were added, nitrogen gas was introduced, and the r...

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Abstract

The invention relates to a synthetic method of a saccharide-containing copolymer with biological specific recognition performance. The synthetic method comprises following steps: in an inert atmosphere, alpha-D-mannose monomer M1 and Grubbs third-generation catalyst are reacted in a solvent; beta-D-galactose monomer M2 is added for reaction; ethyl vinyl ether is added to stop polymerization, and post-treatment is carried out so as to obtain a segmented copolymer containing alpha-D-mannose and beta-D-galactose. Compared with the prior art, the polymer monomer synthetic method is simple and reliable; the obtained polymer structure is linear; the molecular weight is controllable; and the synthetic method can be applied in the fields such as high molecular material and biological medicine engineering.

Description

technical field [0001] The invention relates to the technical field of polymer synthesis, in particular to a method for synthesizing a sugar-containing copolymer with biospecific recognition. Background technique [0002] Sugar is the building block of many natural products in nature, is a common source of energy in living organisms, and plays a vital role in many biological processes. In recent years, the preparation of sugar-containing polymers from sugar-based monomers has become a research hotspot in the fields of chemistry and biology. Sugar-containing polymers refer to functional polymer materials formed by introducing sugar components into polymer molecular chains through different chemical reaction pathways. Due to the presence of sugar groups, this kind of polymer can improve the biocompatibility, hydrophilicity and biodegradability of the polymer, and has a good ability to recognize and bind proteins, so it can be used in biology, medicine, fine chemicals, materia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F293/00G01N21/31
CPCC08F293/00G01N21/31
Inventor 刘美娜刘志峰苗登云邓维朱玉杨文璐王文聪
Owner SHANGHAI INST OF TECH
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