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Method for preparing beta-halogenated ether and beta-halogenated alcohol under catalysis of peroxidase

A peroxidase and peroxidase technology, which is applied in the biological field to achieve the effects of simple raw materials, mild reaction conditions and good stability

Active Publication Date: 2021-10-26
TIANJIN INST OF IND BIOTECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are few reports on the direct synthesis of halogenated ether compounds, and there is no report on the one-step direct conversion of olefins to β-halogenated ether compounds by enzymatic catalysis.

Method used

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  • Method for preparing beta-halogenated ether and beta-halogenated alcohol under catalysis of peroxidase
  • Method for preparing beta-halogenated ether and beta-halogenated alcohol under catalysis of peroxidase
  • Method for preparing beta-halogenated ether and beta-halogenated alcohol under catalysis of peroxidase

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preparation example Construction

[0082] The preparation method of UPO enzyme in the following examples is as follows:

[0083] Pichia pastoris cell culture broth containing rAaeUPO was clarified by centrifugation at 8000 rpm for 2 hours at 4°C. The supernatant was filtered through a 20 μm filter and kept at -80°C. rAaeUPO activity was determined using the ABTS assay in NaPi buffer at pH 5.0;

[0084] Protein Purification: The supernatant was concentrated and dialyzed against 100 mM sodium phosphate, pH 7. AaeUPO was purified in one step using NGC chromatography system (Biorad). Separation was performed on a Q Sepharose FF 30-mL cartridge at a flow rate of 5 mL / min. After 90 mL, the retained protein was eluted with a gradient of 0-50% NaCl in 450 mL, followed by a gradient of 50-100% in 50 mL and 100% NaCl in 75 mL of peroxidase activity followed by an H 2 o 2 Oxidation in the presence of ABTS, appropriate fractions were pooled, concentrated and dialyzed against 100 mM sodium phosphate buffer (pH 7). Pur...

Embodiment 1

[0085] Embodiment 1, the preparation of compound 1-bromo-2-ethoxycyclohexane:

[0086]

[0087] In a 100mL reaction flask, add 31.5mL of pH=6 phosphate buffer solution (sodium dihydrogen phosphate 100 mM), add absolute ethanol (13.5mL) to the above buffer solution, and then sequentially add 0.93mL with a mass fraction of 30 % hydrogen peroxide solution (concentration is 5.38mol / L, concentration in the reaction system is 100mM), 0.59g potassium bromide and 0.820g cyclohexene, finally add 150μL VCPO enzyme (concentration of raw material enzyme is 13.5mg / mL, reaction The enzyme concentration in the system is 500nM). After reacting for about 3 hours, 0.59g potassium bromide, 0.93mL hydrogen peroxide (concentration: 5.38mol / L, concentration in the reaction system: 100mM) and 0.820g cyclohexene were added for a total of three times. Add in separate batches to ensure maximum catalytic activity of the enzyme.

[0088] The above reaction system was stirred and reacted at 30°C for ...

Embodiment 2

[0089] Embodiment 2, the preparation of compound (2-bromo-1-propoxyethyl) benzene:

[0090]

[0091]In a 100mL reaction flask, add 31.5mL of phosphate buffer solution (same pH=6 as above), then add 13.5mL of absolute ethanol to dissolve in the buffer solution, and then add 0.93mL of 30% hydrogen peroxide solution in sequence (Concentration is 5.38mol / L, the concentration in the reaction system is 100mM), 0.59g potassium bromide and 0.16g styrene, finally add 150μL VCPO enzyme (the same as the above enzyme concentration is 13.5mg / mL, the enzyme concentration in the reaction system is 500nM). After reacting for about 3 hours, 0.59 g of potassium bromide, 0.93 mL of hydrogen peroxide (concentration: 5.38 mol / L) and 0.16 g of styrene were added three times in total.

[0092] The above reaction system was stirred and reacted in a water bath at 30°C for 9 hours, then the reaction was terminated, and 100 mL of ethyl acetate was added for extraction twice in total. The organic pha...

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Abstract

The invention discloses a method for preparing beta-halogenated ether and beta-halogenated alcohol through catalysis of peroxidase. The method comprises the following steps: adding hydrogen peroxide, halide salt and olefin as shown in a formula III into a buffer solution, finally adding peroxidase, and reacting to obtain the beta-halogenated alcohol as shown in a formula I; and also adding alcohol as shown in a formula IV into the reaction system to obtain the beta-halogenated ether as shown in a formula II; in the formula I, the formula II, a formula III and the formula IV, R1 is alkyl, phenyl, substituted phenyl, aryl or substituted aryl, R2 is hydrogen, alkyl, phenyl, substituted phenyl, aryl or substituted aryl, wherein R1 and R2 are connected to form a naphthenic base, and R3 is alkyl, phenyl, substituted phenyl, aryl or substituted aryl. According to the invention, the raw materials are simple and easy to obtain, the reaction condition is mild, the operation is simple and convenient, the used solvent is water, and compared with a conventional organic solvent, the method is greener and more environmentally friendly.

Description

technical field [0001] The invention relates to a method for preparing β-halogenated ether and β-halogenated alcohol catalyzed by peroxidase, which belongs to the field of biotechnology. Background technique [0002] Halogenated ether compounds are widely used. Several general anesthetic drugs commonly used in the market today, such as sevoflurane and isoflurane, contain halogenated ether structural units. For example, sevoflurane is one of the most widely used general anesthetic drugs, which has the advantages of low metabolic rate, less stimulation and rapid elimination. In 1981, Coon Clifford L et al. used 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as raw material, reacted with paraformaldehyde in excess hydrogen fluoride gas and fuming sulfuric acid Synthesis of sevoflurane. In this reaction, hydrogen fluoride is a poisonous gas with a pungent smell, which is expensive and causes environmental pollution, and oleum is a hazardous chemical, which has strong irritation and...

Claims

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Application Information

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IPC IPC(8): C12P7/02C12P7/00C12N9/08
CPCC12P7/02C12P7/00C12N9/0065C12Y111/01
Inventor 张武元陈少航孙周通马延和
Owner TIANJIN INST OF IND BIOTECH CHINESE ACADEMY OF SCI
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