Application of linker of polyethylene glycol and fat-soluble compounds in biological catalysis

A fat-soluble compound, polyethylene glycol technology, which is applied in the application field of linker in biocatalysis, can solve the problems of substrate solubility and cell/enzyme activity and stability being difficult to take into account at the same time, so as to improve the reaction rate. And the effect of separation and purification efficiency, improving transformation efficiency, and improving solubility

Inactive Publication Date: 2011-09-07
TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the media systems currently researched and developed are difficult to balance between substrate solubility and cell / enzyme activity and stability.

Method used

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  • Application of linker of polyethylene glycol and fat-soluble compounds in biological catalysis
  • Application of linker of polyethylene glycol and fat-soluble compounds in biological catalysis
  • Application of linker of polyethylene glycol and fat-soluble compounds in biological catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Preparation of 3-oxooleanolic acid-28-(4-methylpolyethylene glycol carboxylate)-benzyl ester

[0045]

[0046] Synthetic route of 3-oxooleanolic acid-28-(polyethylene glycol monoester 4-carboxylate)-benzyl ester

[0047] (1) Preparation of 4-bromomethylbenzoyl chloride: add 4-bromomethyl-benzoic acid (2.15g 10mmol) and toluene (10ml) in a flask, slowly add oxalyl chloride (2.97ml 35mml) dropwise, and stir at room temperature 10min, heated and stirred at 50°C for 3h. After the reaction was completed, it was evaporated to dryness under reduced pressure for later use.

[0048] (2) Preparation of 4-bromomethylbenzoic acid polyethylene glycol monoester: add mPEG (5g 2.5mmol) and toluene (20ml), and reflux for 24h. After the reaction was completed, the toluene was evaporated to dryness under reduced pressure to obtain a yellow oily solid, which was washed three times with 20 ml of anhydrous ether, filtered, and dried in vacuo to obtain a white powder (4.97 g 2.27 mmol yi...

Embodiment 2

[0052] Preparation of 3-methylpolyethylene glycol succinyl oleanolic acid

[0053]

[0054] Synthetic route of 3-methylpolyethylene glycol succinyl oleanolic acid

[0055] (1) Synthesis of 1,4-succinic acid methyl polyethylene glycol monoester: add m-PEG (20g 10mmol), succinic anhydride (10g 10mmol), pyridine (8ml 10mmol) and chloroform in a flask (50ml), reflux for 48h. After the reaction was completed, the chloroform was evaporated to dryness under reduced pressure, and the precipitate was dissolved in a saturated sodium bicarbonate solution (200ml) in an ice bath, and the insoluble matter was filtered off, extracted twice with ethyl acetate (20ml) (removing pyridine), and the filtrate was cooled to Acidify with hydrochloric acid at 0-5°C, adjust PH = 2, extract 3 times with dichloromethane (100ml), dry the organic layer with anhydrous sodium sulfate, evaporate dichloromethane to dryness under reduced pressure to obtain an oily solid, wash with anhydrous diethyl ether (1...

Embodiment 3

[0060] Synthesis of 3-(1-methylpolyethylene glycol monoester-4-succinoyl)-cholesterol

[0061]

[0062] Synthetic route of 3-(1-methylpolyethylene glycol monoester-4-succinyl)-cholesterol

[0063] (1) Synthesis of 3-(1-methylpolyethylene glycol monoester-4-succinyl)-cholesterol: add m-PEG-DA (4.2g2mmol), cholesterol (3.87g 10mmol) and three Methyl chloride (10ml), oxalyl chloride (0.425mmol) was slowly added dropwise, stirred at room temperature for 10min, and heated to reflux for 10h. After the reaction was completed, the solvent was evaporated to dryness under reduced pressure.

[0064] (2) The precipitate was washed three times with saturated sodium bicarbonate solution (100ml), then washed twice with anhydrous ether (100ml), filtered,

[0065] (3) The obtained crude product was purified by column chromatography (dichloromethane:petroleum ether=1:3), and dried in vacuo to obtain a light yellow solid. (3.45g1.4mmol yield 70%)

[0066] 1 HNMR (CDCl 3 , 400MHz): 2.64(...

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Abstract

The invention relates to application of a linker of polyethylene glycol and fat-soluble compounds in biological catalysis. In the invention, mPEG (methoxy polyethylene glycol) is linked with various fat-soluble compounds such as sterides, triterpene and the like by linking bridges to synthesize mPEG-modified water-soluble derivatives: OS-Z-mPEG. Via the derivatives, the original fat-soluble organic compounds can be completely dissolved in water without adding any cosolvents to perform homogeneous biological conversion or catalysis; and after reaction, by the solvent precipitation characteristic of the mPEG polymer, the converted products are selectively precipitated, filtered and collected from the fermentation liquid, thereby achieving the aims of dissolving the fat-soluble compounds and simplifying separation of the converted products.

Description

technical field [0001] The invention belongs to the field of cosolvents, in particular to the application of a linker of polyethylene glycol and a fat-soluble compound in biocatalysis. Background technique [0002] OECD pointed out that "biocatalytic technology is the most promising technology for sustainable industrial development". In recent years, with the rapid development and mutual cross-penetration of biotechnology and organic synthetic chemistry, biocatalysis has gradually become a standard organic synthesis method. Compared with chemical synthesis technology, biocatalysis has high selectivity and mild reaction conditions. , environmental friendliness and other characteristics, it is a hot spot and frontier direction of biotechnology and organic synthesis research, and has been widely used in medicine, fine chemicals, food additives, daily chemicals, materials and other fields. [0003] Biocatalysts include biological enzymes and microbial cells. The biological enzy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/48C12P33/00C12R1/645
Inventor 孙华郁彭赵旭周瑶
Owner TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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