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Preparation method of glycopolymer with lateral chains containing heterogeneous sugar units

A sugar unit and polymer technology, which is applied in the synthesis field of sugar-containing polymers to achieve the effects of regular structure, narrow molecular weight distribution and stable synthesis method

Active Publication Date: 2019-10-08
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the combination of click chemistry and RAFT technology has made some progress in the preparation of structurally controllable sugar-containing polymers, the development of efficient polymer synthesis methods to prepare sugar-containing polymers is still a problem and challenge for polymer scientists.

Method used

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  • Preparation method of glycopolymer with lateral chains containing heterogeneous sugar units
  • Preparation method of glycopolymer with lateral chains containing heterogeneous sugar units
  • Preparation method of glycopolymer with lateral chains containing heterogeneous sugar units

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] The synthesis of poly-A-Man-OH and poly-A-Man-Man-OH poly-A-Man-Man-OH polymers containing heterogeneous sugar units in the side chain, the specific steps are as follows:

[0090] 1. Synthesis of Compound 1

[0091] Weigh 2-amino-2-methyl-1,3-propanediol (20.0g, 0.19mol) and dissolve it in 200mL (MeOH:t-BuOH=1:1) solution, add dropwise BOC anhydride (57mL, 0.247mol ), reacted at room temperature for 18 h, and after the reaction was completed, the solvent was spin-dried, and recrystallized from ethyl acetate and petroleum ether to obtain 31.9 g of a white solid (Compound 1), with a yield of 82%. 1 H NMR (500MHz, CDCl 3 )δ=4.97(s,1H),3.77(dd,J=11.3,5.4Hz,2H),3.61(dd,J=11.3,7.1Hz,2H),1.69(s,2H),1.44(s,9H ),1.16(s,3H).

[0092] 2. Synthesis of compound 2

[0093] Weigh compound 1 (24.0g, 0.117mol) and dissolve it in 200mL of N,N-dimethylformamide, slowly add propargyl bromide (35.1mL, 0.468mol) dropwise at 0°C, and continue the reaction for 10min. Then add potassium hy...

Embodiment 2

[0114] The synthesis of the sugar-containing polymer poly-A-Man-Glu-OH containing heterogeneous sugar units in the side chain, the specific steps are as follows:

[0115] 1. Synthesis of Compound 1

[0116] As in step 1 in Example 1.

[0117] 2. Synthesis of compound 2

[0118] As in step 1 in Example 1.

[0119] 3. Synthesis of α-D-mannose and β-D-glucose heterogeneous sugar addition compound BOC-A-Man-Glu-OAc

[0120] Take BOC-A-Man-OAc (0.95g, 1.45mmol) and β-D-glucose azide compound (0.6g, 1.6mmol) and dissolve in 10mL of (t-BuOH:H 2 O=1:1) in the mixed solvent, then add the catalyst copper sulfate pentahydrate (0.18g, 0.73mmol) and sodium ascorbate (0.29g, 1.45mmol), after stirring at room temperature for 2h, dichloromethane and saturated salt Extracted with water, the collected organic phase was dried with anhydrous sodium sulfate, and the product was subjected to column chromatography to obtain 1.21 g of a white solid (BOC-A-Man-Glu-OAc), with a yield of 81%. The h...

Embodiment 3

[0128] The synthesis of the poly-A-Man-Gal-OH poly-A-Man-Gal-OH polymer containing heterogeneous sugar units in the side chain, the specific steps are as follows:

[0129] 1. Synthesis of Compound 1

[0130] As in step 1 in Example 1.

[0131] 2. Synthesis of compound 2

[0132] As in step 1 in Example 1.

[0133] 3. Synthesis of α-D-mannose and β-D-galactose heterogeneous sugar addition compound BOC-A-Man-Gal-OAc

[0134] In the same synthesis method as BOC-A-Man-Glu-OAc, BOC-A-Man-OAc reacts with β-D-galactose azide to prepare BOC-A-Man-Gal-OAc, and obtains a white solid with a yield of was 66%. The hydrogen spectrum and carbon spectrum of BOC-A-Man-Gal-OAc are as follows Figure 24 with Figure 25 shown. 1 H NMR (500MHz, CDCl 3)δ=7.79-7.72(m,2H),6.02(d,J=8.2Hz,1H),5.88-5.80(m,3H),5.49-5.42(m,2H),5.29(t,J=9.1Hz ,2H),5.21(d,J=7.2Hz,1H),4.91(s,1H),4.52(d,J=20.1Hz,5H),4.24(s,2H),4.14-3.90(m,4H) ,3.82(s,1H),3.54(d,J=8.6Hz,1H),3.45(dd,J=17.1,10.6Hz,3H),3.31(d,J=9.3Hz,1H...

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Abstract

The invention relates to a preparation method of glycopolymer with lateral chains containing heterogeneous sugar units. The preparation method includes: using 2-amino-2-methyl-1,3-propanediol as the raw material, using BOC to perform amino protection, then allowing the 2-amino-2-methyl-1,3-propanediol to have Williamson etherification reaction with propargyl bromide to prepare a compound with terminal alkyne, using an acetyl protected carbohydrate compound containing azido as the raw material to prepare a compound containing heterogeneous sugar through click chemical reaction, removing BOC protection, polymerizing with RAFT, using modification after polymerization to prepare glycopolymer with lateral chains containing heterogeneous sugar units, and then removing OAc protection to prepare glycopolymer containing heterogeneous sugar units. Compared with the prior art, the preparation method is simple in polymer monomer synthesizing method and controllable in polymer lateral chain structure, and the prepared glycopolymer is controllable in molecular weight, narrow in molecular weight distribution, good in water solubility and applicable to fields such as high polymer materials and biological medicine.

Description

technical field [0001] The invention relates to the synthesis of a sugar-containing polymer, in particular to a preparation method for a sugar-containing polymer containing heterogeneous sugar units in the side chain. Background technique [0002] Sugar is involved in many behaviors in the living body, including cell recognition, cell proliferation, signal transmission, and pathogen infection. It has become a hot spot in the field of scientific research. Using the specific recognition of sugar and protein can improve the effect of treating diseases. However, the interaction between a single ligand and the protein is limited, and multivalent ligands are needed to enhance the interaction with the receptor. However, sugar-containing polymers existing in nature are not only difficult to purify but also have complex structures, which greatly limits their utilization. Synthetic sugar-containing polymers have the advantages of clear structure and controllable molecular weight, and...

Claims

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Application Information

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IPC IPC(8): C08F120/22C08F8/32C07H19/056C07H1/00
CPCC07H1/00C07H19/056C08F8/32C08F120/22C08F2438/03
Inventor 刘美娜苗登云刘志峰王星又邓维元渊美毛丹
Owner SHANGHAI INST OF TECH
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