Synthesis method of highly ordered dendronized heterogeneous glycopolymer containing various glycosyl groups

A highly ordered, synthetic method of technology, applied in the field of synthesis of dendritic heterogeneous sugar-containing polymers, can solve the problem of inability to accurately simulate the strong recognition ability of natural polysaccharides, and cannot meet the needs and functions of sugar-containing polymers for diversification and functionalization. problems such as difficulty in obtaining high yield

Active Publication Date: 2021-06-11
SHANGHAI INST OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004]The limited functionality of sugar-containing monomers and the high yield that is difficult to obtain, currently, the direct polymerization of sugar-containing monomers to obtain high-purity heterosaccharide polymers cannot satisfy The demand for diversification and functionalization of sugar-containing polymers
Many of these synthetic glycopolymers contain only one class of sugar residues, which is very different from the inherent heterogeneity of biological systems, resulting in the inability of glycopolymers to accurately mimic the strong recognition ability of natural polysaccharides.

Method used

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  • Synthesis method of highly ordered dendronized heterogeneous glycopolymer containing various glycosyl groups
  • Synthesis method of highly ordered dendronized heterogeneous glycopolymer containing various glycosyl groups
  • Synthesis method of highly ordered dendronized heterogeneous glycopolymer containing various glycosyl groups

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] 1. Synthesis of Compound 1

[0071]Heavy vapor triethylamine (0.6 mL, 4.0 mmol) was added dropwise to pentafluorophenol (0.62 g, 3.37 mmol) in anhydrous DCM solution (6 mL), and acryloyl chloride was added dropwise after stirring 15 min. (0.3 ml, 4.0 mmol), continuously stirred at 0 ° C for 30 min, and the reaction was at room temperature for 2 h. After completion of the reaction, the reaction solution was diluted with DCM, filtered, DCM washing filter, and the filtrate was washed twice with saturated brine. The organic phase was dried over anhydrous sodium sulfate, filtered, spurly removed the solvent, and obtained a colorless oil product PFPA (1,0.6 g, yield 70%) was obtained by silica gel column chromatography (PE).

[0072] Refer to the nuclear magnetic hydrogen spectrum of the obtained compound 1 figure 1 .

[0073] 1 H NMR (500MHz, CDCL 3 : δ = 6.72 (D, J = 17.0 Hz, 1H), 6.37 (DD, J = 17.5, 10.5 Hz, 1H), 6.18 (D, J = 10.5 Hz, 1H). 19 F NMR (470MHz, CDCL 3 : δ = -152.5...

Embodiment 2

[0079] 1. Synthesis of Compound 1 (PFPA) and Compound 2 (PPFPA) is as in Example 1

[0080] 2. Preparation of sugar polymer P1-P8

[0081] In a nitrogen-filled glove box, Compound 2 (50 mg, 0.21 mmol), and branned glycosamine (S1-S8, 0.10 mmol), DMAP (12.8 mg, 0.10 mmol) were added to the glass bottle, then add anhydrous DMF (4 mL) dissolved, the mixture was stirred at 65 ° C for stirring at a glove box filled with nitrogen 24 h. After completion, the reaction liquid was subjected to diethyl ether three times, centrifuged, and dried overnight at 40 ° C vacuum to give a sugar-containing polymer protected by brown powder OAC (corresponding to P1-P8 according to S1-S8), yield at 55% - Between 58%.

[0082] The prepared sugar-containing polymer P1-P8 nuclear magnetic hydrogen spectrum is respectively Figure 3 to 10 Indicated.

[0083] 3. Preparation of branched sugar-containing polymer P9-P16

[0084] At room temperature, Meona (0.48 mmol) was added dropwise to the sugar-containing po...

Embodiment 3

[0089] 1. Synthesis of Compound 1 (PFPA) and Compound 2 (PPFPA) is as in Example 1

[0090] 2. Preparation of sugar-containing polymer P1-P8 and P9-P16 is as in Example 2

[0091] 3. Turbidity method Test the specific identification effect of branches containing sugar-containing polymer P9-P16 and knife bean protein A (con a)

[0092] The CON A and the sugar polymer were dissolved in the HEPES buffer of pH = 7.4. First, 238 mgHepes is dissolved in 10 ml of deionized water, and the pH = 7 was adjusted with NaOH, and then 62.5 mg MnCl 2 , 55.5mg CaCl 2 480 mg NaCl was dissolved with 15 ml of deionized water and added to the HEPES aqueous solution to adjust the pH, and 100 ml of volumetric flask was added, filtered with the filtration membrane before using the filter membrane to prepare 0.01 m HEPES buffer. Then, 1 mg / ml of CON A solution was configured with a buffer, and 1 mg / ml of sugar-containing polymer solution. After adding 0.40 ml of CON A solution (1 mg / ml), after addin...

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Abstract

The invention relates to a synthesis method of a highly ordered dendronized heterogeneous glycopolymer containing various glycosyl groups. The method comprises the following steps: (1) adding anhydrous triethylamine into a dichloromethane solution of pentafluorophenol under an ice bath condition, then adding acryloyl chloride for reaction, and after the reaction is finished, washing, drying and purifying to obtain a compound PFPA; (2) carrying out polymerization reaction on the compound PFPA, a chain transfer agent and an initiator to obtain a polymer pPFPA; (3) mixing the polymer pPFPA with dendronized glycosamine, and carrying out ammonolysis reaction to obtain a glycopolymer; and (4) adding the glycopolymer into a sodium methoxide/methanol solution to react, and purifying after the reaction is finished, thereby obtaining the target product, namely the dendronized heterogeneous glycopolymer containing various glycosyl groups. Compared with the prior art, the method has the advantages that the advantages of RAFT polymerization and post-modification are combined, the glycopolymer with the ordered structure is obtained, particularly the regular heterogeneous glycopolymer is obtained, and a universal platform and the like are provided for preparation of the functional glycopolymer.

Description

Technical field [0001] The present invention belongs to the field of sugar-containing polymer synthesis, and it is directed to a synthetic method of highly orderly a plurality of glycosyl dendridic acid-containing polymers. Background technique [0002] High binding progenitors produced by multivalent sugar and aggregate are referred to as "sugar cluster effects". This type of sugar cluster effect has been widely studied. Since the complexity of natural polysaccharides is not conducive to direct synthesis and replication, a series of sugar-based natural polysaccharide brackets are generated to study the specific identification of sugar and lectin. These controllable natural polysaccharide brackets are not only conducive to large-scale synthesis, but also adapt to the desired biological activities and explore specific biological processes. Among them, the sugar-containing polymer has a large regulatable range on the chain glycogen based, binding group spacing, linkage function, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F120/22C08F2/38C08F8/30
CPCC08F120/22C08F2/38C08F8/30C08F2438/03Y02P20/55
Inventor 王星又刘美娜王梦彤周志叶飞何子怡杨玉莹
Owner SHANGHAI INST OF TECH
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