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Method for reducing nitrocompound through biocatalysis

A technology for nitro compounds and biocatalysis, which is applied in the field of biocatalytic reduction of nitro compounds, can solve the problems of difficult separation and treatment of products, potential safety hazards, and heavy use of heavy metals, etc., achieves high-throughput and rapid nitro reduction reaction, and is easy to operate. Fast, broad substrate availability effects

Pending Publication Date: 2020-05-08
PORTON FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of method produces many by-products, which may destroy other structures of the compound, and requires a large amount of heavy metals in the reaction, and the post-treatment is very cumbersome. The product is difficult to separate and handle, and there is pollution.

Method used

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  • Method for reducing nitrocompound through biocatalysis
  • Method for reducing nitrocompound through biocatalysis
  • Method for reducing nitrocompound through biocatalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Take 0.25g m-nitropropiophenone (3-nitropropiophenone), 10mL dimethyl sulfoxide (10% v / v), 2g glucose (20g / L), 1g olefin reductase ERED-103, 0.1g glucose Dehydrogenase, 1mL Triton X-100, 5mg NADP + After mixing with 89mL sodium phosphate buffer solution (100mM, pH7.0), react at 30°C with a shaker at 300r / min for 24h. After the reaction, take a sample and add ethanol, centrifuge, and collect the filtrate by filtration to prepare Hydroxylamine compound. LC-MS is used for analysis, and it is measured that the conversion rate of the nitro compound into the hydroxylamine compound is 95%.

[0045]

[0046] In this embodiment, glucose dehydrogenase, NADP + , Glucose is mainly used for the preparation and regeneration of NADPH (reduced coenzyme II), to construct an efficient coenzyme NADPH regeneration system; NAD can also be used + , used to prepare coenzyme NADH and construct its regeneration system.

[0047] In this embodiment, the cosolvent can also be isopropanol, 1...

Embodiment 2

[0050] Take 0.25g p-nitrotoluene (4-nitrotoluene), 10mL dimethyl sulfoxide (10% v / v), 2g glucose (20g / L), 1g olefin reductase ERED-103, 0.1g glucose dehydrogenation Enzyme, 1mL Triton X-100, 5mg NADP + After mixing with 89mL sodium phosphate buffer solution (100mM, pH7.0), react at 30°C with a shaker at 300r / min for 24h. After the reaction, take a sample and add ethanol, centrifuge, and collect the filtrate by filtration to prepare Hydroxylamine compound. The hydroxylamine compound is 4-(hydroxyamino)toluene.

[0051]

[0052] In this embodiment, glucose dehydrogenase, NADP + , Glucose is mainly used for the preparation and regeneration of NADPH (reduced coenzyme II), to construct an efficient coenzyme NADPH regeneration system; NAD can also be used + , used to prepare coenzyme NADH and construct its regeneration system.

[0053] In this embodiment, the cosolvent can also be isopropanol, 1,3-dioxane or ethyl acetate; the buffer can also be trimethylolmethylamine-hydroch...

Embodiment 3

[0056] Take 0.25g 1-chloro-2-methyl-3-nitrobenzene, 10mL dimethyl sulfoxide (10% v / v), 2g glucose (20g / L), 1g olefin reductase ERED-103, 0.1g glucose Dehydrogenase, 1mL Triton X-100, 5mg NADP + After mixing with 89mL sodium phosphate buffer solution (100mM, pH7.0), react at 30°C with a shaker at 300r / min for 24h. After the reaction, take a sample and add ethanol, centrifuge, and collect the filtrate by filtration to prepare Hydroxylamine compound. The hydroxylamine compound is 3-chloro-2-methylphenylhydroxylamine.

[0057]

[0058] In this embodiment, glucose dehydrogenase, NADP + , Glucose is mainly used for the preparation and regeneration of NADPH (reduced coenzyme II), to construct an efficient coenzyme NADPH regeneration system; NAD can also be used + , used to prepare coenzyme NADH and construct its regeneration system.

[0059] In this embodiment, the cosolvent can also be isopropanol, 1,3-dioxane or ethyl acetate; the buffer can also be trimethylolmethylamine-hy...

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Abstract

The invention provides a method for reducing nitrocompound through biocatalysis. A coenzyme is used as a hydrogen donor, olefin reductase is used as a catalyst, the nitrocompound is subjected to catalytic reduction, and a hydroxylamine compound or an amine compound is generated. The method for reducing the nitrocompound through biocatalysis provided by the invention replaces a conventional methodfor chemically reducing the nitrocompound which is complex, dangerous and polluted in product extraction, the olefin reductase which can be obtained through purchase from the market or prepared by oneself is used as the catalyst, and a quick, simple and effective scheme for reducing the nitrocompound by a biocatalysis method can be established; and the nitrocompound is reduced into the stable hydroxylamine compound or the amine compound, the method has broad substrate applicability, and a high-flux and rapid nitroreduction reaction can be realized.

Description

technical field [0001] The invention relates to the field of preparation of amine and hydroxylamine compounds, in particular to a method for biocatalytically reducing nitro compounds. Background technique [0002] The reduction of nitro compounds, especially the synthesis of different alkyl aromatic amines and aryl hydroxylamine compounds is a common reaction category in chemical synthesis and chemical production. Traditionally, such reactions are accomplished by reduction of reducing metal powders such as iron and zinc or catalytic hydrogenation under high pressure. However, this type of method produces many by-products, which may damage other structures of the compound, and requires a large amount of heavy metals in the reaction, which makes the post-treatment very cumbersome, and the product is difficult to separate and handle, and there is pollution. [0003] Therefore, in order to avoid the pollution and dangerous operation of chemical methods, it is necessary to provi...

Claims

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Application Information

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IPC IPC(8): C12P13/00C12P17/12
CPCC12P13/001C12P17/12
Inventor 周建光李仁结乐庸堂孟枭
Owner PORTON FINE CHEM
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