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Double-enzyme one-pot synthesis method of 2,3-dimethyl-5alkylamino-1,4-benzoquinone

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

Inactive Publication Date: 2018-02-02
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Double-enzyme one-pot synthesis method of 2,3-dimethyl-5alkylamino-1,4-benzoquinone
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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 solution, added ammonium sulfate under slow stirring at 150rpm at 4°C to make the concentration 0.5kg / L, continued stirring 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 agg...

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, and 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 aggregat...

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Abstract

The invention relates to a double-enzyme one-pot synthesis method of 2,3-dimethyl-5alkylamino-1,4-benzoquinone. By the utilization of a crosslinked laccase / lipase aggregation system for catalyzing phenol oxidation / C-N cross-coupling cascade reaction, 2,3-dimethyl-5alkylamino-1,4-benzoquinone is prepared. laccase catalyzes 2,3-dimethylhydroquinone oxidation to generate 2,3-dimethyl-p-benzoquinone,and lipase catalyzes 2,3-dimethyl-p-benzoquinone and fatty primary amines for the C-N cross-coupling reaction so as to prepare the product. The yield reaches 95% and above. According to the technologyfor concerted catalysis of phenol oxidation / C-N cross-coupling reaction by the utilization of lipase and laccase, yield of the product is raised by about 200% in comparison with single laccase catalysis; and the method has higher selectivity than a traditional chemocatalysis method, and by-products are less. The method of the invention 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, thereby obtaining The product 2,3-dimethyl-5-alkylamino-1,4-benzoquinone. Background technique [0002] Mitomycin is a class of antibiotics with anti-tumor 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. ...

Claims

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Application Information

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Patent Type & Authority Applications(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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