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A method for synthesizing 2,3-dimethyl-5-alkylamino-1,4-benzoquinone in one pot with two enzymes

A technology of dimethyl hydroquinone and dimethyl, which is applied in the field of double-enzyme one-pot synthesis of 2,3-dimethyl-5-alkylamino-1,4-benzoquinone, can solve the problem of affecting C-N cross-coupling reaction , low efficiency of aminoquinone compounds, low product yield and other problems, to solve the problem of inhibition of benzoquinone products, to avoid the effect of relatively expensive and easy-to-operate reaction conditions

Inactive Publication Date: 2021-03-02
QINGDAO UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a single laccase can mediate the synthesis of aminoquinones, there are still obvious shortcomings: poor selectivity, many by-products, and low product yield
[0005] In order to solve the above problems, we have conducted a lot of research and found that p-benzoquinone produced by laccase-catalyzed oxidation of phenol has a large product inhibitory effect on laccase, which seriously affects its subsequent catalysis of C-N crossover between p-benzoquinone and amine donors. The coupling reaction is an important reason for the low efficiency of the synthesis of aminoquinones catalyzed by a single laccase

Method used

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  • A method for synthesizing 2,3-dimethyl-5-alkylamino-1,4-benzoquinone in one pot with two enzymes
  • A method for synthesizing 2,3-dimethyl-5-alkylamino-1,4-benzoquinone in one pot with two enzymes

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Embodiment 1

[0033] A method for synthesizing 2,3-dimethyl-5-alkylamino-1,4-benzoquinone in one pot with two enzymes, the specific steps are as follows: (1) Preparation of Myceliophthora thermophila laccase / Aspergillus niger lipase Double-enzyme cross-linking enzyme aggregates, the process is as follows: 1.0Kg Myceliophthora thermophila laccase enzyme powder (≥800U / g) and Aspergillus niger lipase enzyme powder (≥800U / g) mixture (ratio of enzyme activity 1:10), dissolved in 6L of pH 7.0 phosphate buffer solution, added ammonium sulfate under slow stirring at 150rpm at 4°C to make the concentration 0.3kg / L, continued to stir for 30min, and added the cross-linking agent glutaraldehyde Make the concentration 0.2%, cross-link for 2 hours, centrifuge the mixed solution at 4°C, 5000×g for 10 minutes, remove the supernatant, wash the precipitate with deionized water, and freeze-dry to obtain Myceliophthora thermophila laccase / Aspergillus niger The enzyme lipase double enzyme cross-links enzyme agg...

Embodiment 2

[0036] A method for synthesizing 2,3-dimethyl-5-alkylamino-1,4-benzoquinone in one pot with two enzymes, the specific steps are as follows: (1) Preparation of Myceliophthora thermophila laccase / Aspergillus niger lipase Double-enzyme cross-linking enzyme aggregates, the process is as follows: 0.5Kg Myceliophthora thermophila laccase enzyme powder (≥800U / g) and Aspergillus niger lipase enzyme powder (≥800U / g) mixture (ratio of enzyme activity 1:9), dissolved in 3L of pH 7.0 phosphate buffer, added ammonium sulfate under slow stirring at 150rpm at 4°C to make the concentration 0.5kg / L, continued to stir for 30min, and added the cross-linking agent glutaraldehyde Make the concentration 0.3%, cross-link for 2 hours, centrifuge the mixed solution at 4°C, 5000×g for 10 minutes, remove the supernatant, wash the precipitate with deionized water, and freeze-dry to obtain Myceliophthora thermophila laccase / Aspergillus niger The enzyme lipase double enzyme cross-links enzyme aggregates. ...

Embodiment 3

[0039] A method for synthesizing 2,3-dimethyl-5-alkylamino-1,4-benzoquinone in one pot with two enzymes, the specific steps are as follows: (1) Preparation of Myceliophthora thermophila laccase / Aspergillus niger lipase Double-enzyme cross-linking enzyme aggregates, the process is as follows: 3.0Kg Myceliophthora thermophila laccase enzyme powder (≥800U / g) and Aspergillus niger lipase enzyme powder (≥800U / g) mixture (ratio of enzyme activity 1:5), dissolved in 20L of pH 7.0 phosphate buffer solution, added ammonium sulfate under slow stirring at 150rpm at 4°C to make the concentration 0.4kg / L, continued stirring for 30min, and added the cross-linking agent glutaraldehyde Make the concentration 0.1%, cross-link for 1 hour, centrifuge the mixed solution at 4°C, 5000×g for 10 minutes, remove the supernatant, wash the precipitate with deionized water, and freeze-dry to obtain Myceliophthora thermophila laccase / Aspergillus niger The enzyme lipase double enzyme cross-links enzyme agg...

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Abstract

The invention relates to a method for synthesizing 2,3-dimethyl-5-alkylamino-1,4-benzoquinone by a double-enzyme one-pot method, which utilizes a cross-linked laccase / lipase aggregate system to catalyze phenol oxidation / C-N Preparation of 2,3-dimethyl-5-alkylamino-1,4-benzoquinone by cross-coupling series reaction. Among them, laccase catalyzes the oxidation of 2,3-dimethylhydroquinone to generate 2,3-dimethyl-p-benzoquinone, and at the same time, lipase catalyzes the generation of C- N cross-coupling reaction to prepare the product with a yield of more than 95%. This process utilizes lipase and laccase to synergistically catalyze the phenol oxidation / C-N cross-coupling reaction, which increases the product yield by about 200% compared with that catalyzed by a single laccase. At the same time, it has higher selectivity and fewer by-products than traditional chemical catalytic methods. , is a green and environmentally friendly synthesis method.

Description

technical field [0001] The invention belongs to the technical field of enzyme catalysis, and specifically relates to a method for synthesizing 2,3-dimethyl-5-alkylamino-1,4-benzoquinone by a double-enzyme one-pot method, that is, using laccase to catalyze 2,3-dimethyl Hydroquinone is oxidized to generate 2,3-dimethyl-p-benzoquinone. At the same time, under the same conditions, lipase catalyzes the C-N cross-coupling reaction between 2,3-dimethyl-p-benzoquinone and aliphatic primary amines to obtain The product 2,3-dimethyl-5-alkylamino-1,4-benzoquinone. Background technique [0002] Mitomycin is a class of antibiotics with antitumor activity, and its main member is mitomycin C (mitomycinC, MMC), the structure of which is shown in formula 1. MMC has a strong anti-tumor effect, and is widely used in the treatment of tumors in the stomach, pancreas, colon, rectum, breast, lung and other parts in clinical practice, but its toxic and side effects are relatively large. The antit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P13/00
CPCC12P13/001
Inventor 张媛媛鲁佩玉李涛孙青华王繁业
Owner QINGDAO UNIV OF SCI & TECH
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