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Chiral supramolecular hydrogel element with optimized structure, preparation method and application thereof

A supramolecular hydrogel, chiral amino acid technology, applied in biochemical equipment and methods, general culture methods, microorganisms, etc., can solve the problems of difficult stabilization and enhancement of chiral supramolecular hydrogels, and achieve easy structural Disintegration problems, increased intermolecular forces, effects of simple equipment

Active Publication Date: 2021-07-27
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the basis of the previous invention patents, by optimizing the hydrophobic base of the central core, when the molecule self-assembles, due to the larger π-bond conjugated structure in the molecular center, the intermolecular π-π interaction is greatly enhanced, and the chiral amino acid is coordinated Hydrogen bonding between amide bonds can obtain supramolecular hydrogel materials with more stable chiral assembly structures, and solve the problem that existing chiral supramolecular hydrogels are difficult to stabilize

Method used

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  • Chiral supramolecular hydrogel element with optimized structure, preparation method and application thereof
  • Chiral supramolecular hydrogel element with optimized structure, preparation method and application thereof
  • Chiral supramolecular hydrogel element with optimized structure, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1, B-pH (D-PHE-OH) shown in Formula (I) 2 Preparation

[0048]

[0049] (1) Benophenylel chloride (3.58 g, 13.0 mmol) was dissolved in dry dichloromethane, and added to two-containing methyl alanine methyl esters (6.0 g, 26.1 mmol). Chloromethane and triethylamine (ET 3 In a solution of N, 8.0 mL, 58.3 mmol, stirred at room temperature, stirred and dissolved in ethanol after stirring the solvent, filtered to obtain B-pH (D-Phe-Ome) 2 .

[0050] (2) A NaOH aqueous solution was added to 20 ml of B-pH (D-Phe-OME) 2 (3.46 g, 6.14 mmol) methanol suspension solution, and the aqueous cooled to room temperature was stirred for 24 hours to obtain a clear solution. The gel-shaped precipitate was acidified with EtOAc. The filtration is dried to obtain B-pH (D-Phe-OH) 2 , Nuclear magnetic hydrogen spectrum figure 1 Indicated.

[0051] (3) Preparation of hydrogel: Weigh a certain amount of B-pH (D-PHE-OH) 2 The molecule, add deionized water, after heating to completely dissolv...

Embodiment 2

[0052] Example 2, N-pH (D-PHE-OH) shown in formula (II) 2 Preparation:

[0053]

[0054] (1) 2,6-naphthal chloride (3.27 g, 13.0 mmol) was dissolved in dichloromethane and added to two of D-phenylalanine methyl esters (6.0 g, 26.1 mmol). In a solution of chloromethane and triethylamine (Et3N, 8.0 mL, 58.3 mmol), stirring at room temperature for 24 h, and dissolved in ethanol dissolved after the solvent was evaporated, dried to give B-pH (D-Phe-OME) 2.

[0055] (2) in 20 ml N-pH (D-Phe-OME) 2 (3.30 g, 6.14 mmol) methanol suspension solution, NaOH aqueous solution was added, and the suction solution was subjected to a clear solution after stirring for 24 hours. The gel-shaped precipitate was acidified with EtOAc. Etch dry and dried to get N-pH (D-PHE-OH) 2 , Nuclear magnetic hydrogen spectrum image 3 Indicated.

[0056] (3) Preparation of hydrogel: Weigh a certain amount of N-pH (D-PHE-OH) 2 The molecule, add deionized water, after heating to completely dissolve, deposit cooling, ...

Embodiment 3

[0057] Example 3, Preparation of PDI-PhoH shown in Formula (III:

[0058]

[0059] (1) Dissolve the osmide dimethyl chloride in dichloromethane, adding to a solution containing D-phenylalanine methyl methyl methyl chloride and triethylamine, stirring at room temperature for 24 h , In the ethanol dissolved after the solvent is removed, the dried dried to obtain a PDI- (PHOME) 2 .

[0060] (2) in PDI- (Phome) 2 In the methanol suspension solution, a NaOH aqueous solution was added, and the suction solution was subjected to a clear solution after slow cooling to room temperature for 24 hours. The gel-shaped precipitate was acidified with EtOAc. The filtration was dried to give PDI-PhoH, and the nuclear magnetic hydrogen spectrum is like Figure 5 Indicated.

[0061] (3) Preparation of hydrogel: Weigh a certain amount of PDI-PHOH molecules, add deionized water, after heating to completely dissolve, deposition at room temperature, and translucent hydrogel formation. After scanning ele...

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PUM

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Abstract

The invention discloses a design thought and a preparation method of a chiral supramolecular hydrogel element with an optimized structure, wherein the chiral supramolecular hydrogel takes perylene bisimide, biphenyl, naphthalene ring and other large pi bond conjugated structure-containing hydrophobic groups as a central core, and chiral amino acid elements are symmetrically connected to the two sides of the central core. By optimizing a central core hydrophobic element, during molecular self-assembly, due to a larger pi bond conjugated structure in the molecular center, the intermolecular pi-pi interaction is greatly enhanced, and a supermolecular hydrogel material with a more stable chiral assembly structure can be obtained by cooperating with the hydrogen-bond interaction between chiral amino acid amido bonds.

Description

Technical field [0001] The present invention belongs to the field of chemical synthesis, and more particularly to a method of structural optimized chiral hypertrophogenic gel preparation and application thereof, in particular, to an enhanced gel substrate by increasing the center of the gel base center. Π-π stacked interactions. Using the gel base center core strong π-π conjugate action synergistic hydrogen bonding, a hypertropic hydrogel material having a more stable chiral assembly structure can be obtained, and the existing gel element is solved due to molecules. The assembly structure caused by a weak interaction cannot be stably presented long-term, and the problem of easy to disintegrate. Background technique [0002] The chiral phenomenon is generally in biological and natural boundaries, in the molecular level (such as L-amino acids and D-sugar), nanotic structures (such as DNA, RNA and protein), macro system (such as cylinders and plants), even in galaxies. All exist. Th...

Claims

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Application Information

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IPC IPC(8): C08J3/075C08G83/00C12N5/00
CPCC08J3/075C08G83/008C12N5/0068C12N2533/30C08J2387/00
Inventor 冯传良邢超窦晓秋
Owner SHANGHAI JIAO TONG UNIV
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