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Method for preparing photoactive 2 nitrophenol through catalyzing by utilizing biological enzyme

A technology for catalytic preparation and nitrophenol, applied in biochemical equipment and methods, enzymes, fermentation, etc.

Inactive Publication Date: 2018-01-19
QINGDAO UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The reaction catalyzed by biological enzymes has the characteristics of environmental friendliness and good selectivity, and there is no report on the synthesis of this product by catalyzing biological enzymes

Method used

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  • Method for preparing photoactive 2 nitrophenol through catalyzing by utilizing biological enzyme

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Preparation of pod peroxidase.

[0046] After 10kg of fresh soybean pods are crushed with a pulverizer, the particle size is less than 1mm, add 50L deionized water and soak for 4 hours at room temperature. After the soaking liquid is filtered, the initial extract is obtained, the volume of the initial extract is V; solid sulfuric acid is added to the initial extract during stirring Ammonium, make 45% saturation, and the volume is V1; add 0.3V of pre-cooled acetone while continuing to stir, and centrifuge at 5000 rpm for 10 minutes to obtain supernatant 1, and add solid ammonium sulfate to supernatant 1, According to the volume of V1, add to 75% saturation, centrifuge at 5000 rpm for 10 minutes; at this time, a layer of precipitate will form at the interface between the water phase and the acetone phase, namely precipitation 1, take precipitation 1, add precipitation 1 volume 5 times Dissolve the precipitate 1 in deionized water. After desalting by ultrafiltration, centrifu...

Embodiment 2

[0050] The preparation of (S)-3-(2-fluoro-1-hydroxyethyl)-2,6-2 nitrophenol was catalyzed by pod peroxidase.

[0051] In a 1L reactor, the pod peroxidase of Example 1 was used for the biocatalytic reaction, the substrate was (S)-5-(2-fluoro-1-hydroxyethyl)-2-nitrophenol, the target product It is (S)-3-(2-fluoro-1-hydroxyethyl)-2,6-2 nitrophenol, the ee% of the substrate is 95-99.5%; the reaction medium is a water-organic solvent two-phase system, The aqueous phase is a phosphate buffer with pH 7.0, the organic solvent is isobutanol, the aqueous phase / organic phase=8 / 2, the volume of the reaction solution is 700-750ml, the substrate is dissolved in isobutanol, and then added to the reaction The reaction temperature is 49-51℃, the reaction time is 8-9h, the rotating speed of the stirring blade is 400-450rpm, the concentration of pod peroxidase is 4-5mU / ml, the concentration of substrate is 30mM, NaNO 2 The concentration is 350mM, H 2 O 2 Adopt the feeding method of feeding, add H a...

Embodiment 3

[0054] Use commercially available horseradish peroxidase, lactoperoxidase, chloroperoxidase (from the marine fungus Caldariomyces fumago), and soybean hull peroxidase as catalysts to prepare (S)-3-(2-fluoro -1-Hydroxyethyl)-2,6-2 Nitrophenol.

[0055] The conditions of the catalytic reaction are the same as in Example 2, but the reaction temperature and pH are adjusted according to different enzymes. The experimental results are that the substrate conversion rate is 17-62%, the target product ee% is 95-99.5%, and the target product yield is 14 -49%. It can be seen that only the pod peroxidase has the best catalytic effect.

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Abstract

The invention provides a method for preparing (S)-3-(2-fluoro-1-hydroxyethyl)-2,6-2 nitrophenol through catalyzing by utilizing pod peroxidase. The method provided by the invention has the advantagesof wide source of the used pod peroxidase, low production cost, moderate reaction conditions, environment friendliness, high substrate conversion ratio, good target product selectivity and high yield.

Description

Technical field [0001] The present invention belongs to the technical field of chemical and pharmaceutical engineering, and particularly relates to the preparation of chiral pharmaceutical intermediates (S)-3-(2-fluoro-1-hydroxyethyl)-2,6-2 nitrate catalyzed by pod peroxidase. Phenol-based technology. Background technique [0002] Chiral pharmaceutical intermediate (S)-3-(2-fluoro-1-hydroxyethyl)-2,6-2 nitrophenol is an important pharmaceutical intermediate, which is produced by traditional chemical processes. A large amount of waste acid and acidic wastewater containing organic matter will be produced, which will cause serious environmental pollution, and the resulting products will have almost no selectivity, resulting in waste of raw materials. The existing technology cannot avoid problems such as the corrosion of the equipment caused by strong acid and the potential safety hazards caused by the by-products such as multiple oxidation during the reaction. The resource consump...

Claims

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Application Information

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IPC IPC(8): C12P13/00C12N9/08
Inventor 高鑫姜巍伟李丹
Owner QINGDAO UNIV OF SCI & TECH
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