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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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

However, block copolymerization often

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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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[0047] Example 1

[0048] 1. Synthesis of Precursor G1

[0049] Step 1) Exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride was added to methanol and stirred evenly, cooled to 0°C in an ice-water bath and the temperature was maintained unchanged. Ethanolamine was dissolved in methanol, slowly added, added dropwise for 0.5 h, stirred at low temperature for 15 min, followed by reaction at room temperature for 0.5 h, and finally heated under reflux for 12 h. After the reaction stopped, it was cooled to room temperature for rotary evaporation with H 2 O and CH 2 Cl 2 Extraction and separation, spin-dried to obtain 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'-bicycloethylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP), and the reaction was stirred at room temperature for 24h. After the reaction was stopped, the white solid was removed by filtration, and the filtrate was treated with a silica ...

Example Embodiment

[0070] Example 2

[0071] Into a 10 mL reaction flask, add the heterogeneous sugar-containing monomer NB-Glu-Gal (40 mg, 0.048 mmol) and Grubbs3 rd The catalyst (2.3 mg, 0.002 mmol) was inserted into a dense rubber stopper and sealed with a sealing film. After nitrogen gas was introduced for 10 min, anhydrous N,N'-dimethylformamide (2 mL) was introduced. After stirring the reaction at 65° C. for 24 h, EVE (0.1 mL) was added, and the mixture was stirred at room temperature for 30 min. The reaction 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 is 1.18.

[0072] 9. The specific recognition of sugar-containing polymers and concanavalin A by turbidimetry

[0073] Prepare Concanavalin A (1mg / mL) in HBS buffer solution (HEPES, 10mmol / L), ...

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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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