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Method for preparing glycopolymer through combination of ROMP polymerization and mercapto-alkene addition reaction

An addition reaction and polymer technology, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve complex multi-step operations of block copolymerization, achieve regular structure, controllable structure, and synthetic methods stable effect

Active Publication Date: 2018-11-16
SHANGHAI APPLIED TECHNOLOGIES COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, block copolymerization often requires complex multi-step operations

Method used

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  • Method for preparing glycopolymer through combination of ROMP polymerization and mercapto-alkene addition reaction
  • Method for preparing glycopolymer through combination of ROMP polymerization and mercapto-alkene addition reaction
  • Method for preparing glycopolymer through combination of ROMP polymerization and mercapto-alkene addition reaction

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Experimental program
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Effect test

Embodiment 1

[0048] 1. Synthesis of Precursor G1

[0049] Step 1) Exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride was added into methanol and stirred evenly, cooled to 0°C in an ice-water bath and kept at a constant temperature. Dissolve ethanolamine in methanol, add slowly, dropwise for 0.5h, stir at low temperature for 15min, then react at room temperature for 0.5h, and finally reflux for 12h. After the reaction stopped, carry out rotary evaporation when cooling to room temperature, and use H 2 O and CH 2 Cl 2 Extracted and separated, and spin-dried to obtain a white solid 1;

[0050]Step 2) Dissolve 2,2,5-trimethyl-1,3-dioxane-5-carboxylic acid and 1 in dry dichloromethane, add N,N'-dicycloethylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP), stirred at room temperature for 24 h. After the reaction was stopped, the white solid was removed by filtration, and the filtrate was purified and separated by silica gel chromatography, and finally the white solid 2 was obtained;

...

Embodiment 2

[0071] In a 10 mL reaction vial, add heterogeneous sugar-containing monomer NB-Glu-Gal (40 mg, 0.048 mmol) and Grubbs3 rd The catalyst (2.3mg, 0.002mmol) was stuffed into a dense rubber stopper and sealed with a parafilm, and after passing through nitrogen for 10min, anhydrous N,N'-dimethylformamide (2mL) was passed through. After stirring and reacting at 65° C. for 24 h, EVE (0.1 mL) was added, stirred at room temperature for 30 min, and the reaction liquid was added dropwise to excess methanol for sedimentation. Centrifuge, remove the supernatant, and dry to obtain a tan polymer. The gel permeation chromatogram of PNB-Glu-Gal is shown in Figure 19 . Number average molecular weight Mn=10055, molecular weight M w / M n The distribution index was 1.18.

[0072] 9. Specific recognition of sugar-containing polymers and concanavalin A by nephelometric method

[0073] Prepare concanavalin A (1mg / mL) in HBS buffer solution (HEPES, 10mmol / L), pH=7.4, NaCl (50mmol / L), CaCl 2 (5...

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Abstract

The invention discloses a method for preparing a glycopolymer through combination of ROMP polymerization and a mercapto-alkene addition reaction. The method uses a gradient organic synthesis method, combines a thiol-ene Michael addition, and prepares a norbornene derivative of a heterosaccharide monomer containing non-protective group, and the glycopolymer with controllable molecular weight and narrow molecular weight distribution width can be obtained through ring-opening metathesis polymerization (ROMP). Based on the advantage of thiol-ene Michael addition, a feasible platform and an approach are provided for preparing the heterosaccharide monomer with an ordered side-chain structure; and the heterogeneous glycopolymer prepared by an active ROMP polymerization has important guidance meaning for researching a specific identification mechanism of a sugar unit and agglutinin as well as for developing the functional glycopolymer having a special biological diagnosis function.

Description

technical field [0001] The invention relates to the technical field of synthesis of sugar-containing polymers, in particular to a method for preparing sugar-containing polymers by combining ROMP polymerization and mercapto-ene addition reaction. Background technique [0002] Sugar-containing polymers refer to functional polymer materials formed by introducing sugar units into polymer molecular chains through different chemical reaction pathways. Since glycopolymers have the same "sugar cluster effect" as natural polysaccharides, glycopolymers are endowed with biological functionality with high affinity for specific proteins. For example, the specific recognition of asialin receptors with galactose or galactosamine residues allows the preparation of carrier materials for active liver targeting. Starting from biological materials, mastering the synthesis method of heterogeneous sugar-containing monomers and synthesizing heterogeneous sugar-containing polymers with an ordered ...

Claims

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Application Information

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IPC IPC(8): C08F132/08C07H5/10C07H1/00
CPCC07H1/00C07H5/10C08F132/08Y02P20/55
Inventor 刘美娜叶文玲朱玉邓维吴铜
Owner SHANGHAI APPLIED TECHNOLOGIES COLLEGE
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