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A kind of method for preparing β-haloether and β-halohydrin catalyzed by peroxidase

A technology of peroxidase and peroxidase is applied in the biological field to achieve the effects of being beneficial to large-scale production, simple raw materials and mild reaction conditions

Active Publication Date: 2022-07-26
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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  • A kind of method for preparing β-haloether and β-halohydrin catalyzed by peroxidase
  • A kind of method for preparing β-haloether and β-halohydrin catalyzed by peroxidase
  • A kind of method for preparing β-haloether and β-halohydrin catalyzed by peroxidase

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Experimental program
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Effect test

preparation example Construction

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

[0083] Pichia pastoris cell cultures containing rAaeUPO were 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 by using the ABTS assay in NaPi buffer 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 an NGC chromatography system (Biorad). Separations were performed on Q Sepharose FF 30-mL cartridges at a flow rate of 5 mL / min. After 90 mL, the retained protein was eluted with a 0-50% NaCl gradient in 450 mL, followed by a 50-100% gradient in 50 mL and 100% NaCl in 75 mL peroxidase activity followed by peroxidase activity in H 2 O 2 In the presence of ABTS oxidation, the appropriate fractions were pooled, concentrated and dialyzed against 100 mM sodium phosphate buff...

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

[0088] The above reaction system was st...

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 (the concentration is 5.38mol / L, the concentration in the reaction system is 100mM), 0.59g potassium bromide and 0.16g styrene, and finally 150 μL VCPO enzyme (the same as the above enzyme concentration is 13.5mg / mL, the enzyme concentration in the reaction system is 500nM). After about 3 hours of reaction, 0.59 g of potassium bromide, 0.93 mL of hydrogen peroxide (concentration of 5.38 mol / L) and 0.16 g of styrene were added three times in total.

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

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Abstract

The invention discloses a method for preparing β-halogenated ether and β-halogenated alcohol catalyzed by peroxidase. It includes the following steps: adding hydrogen peroxide, halogen salt, and alkene shown in formula III in the buffer solution, and finally adding peroxidase, and reacting to obtain the β-halohydrin shown in formula I; when the above reaction system When also adding the alcohol shown in formula IV, the β-halogenated ether shown in formula II is obtained; in formula I, formula II, formula III, and formula IV, R 1 is alkyl, phenyl, substituted phenyl, aryl or substituted aryl; R 2 is hydrogen, alkyl, phenyl, substituted phenyl, aryl or substituted aryl; wherein, also includes R 1 and R 2 linked as cycloalkyl; R 3 is alkyl, phenyl, substituted phenyl, aryl, or substituted aryl. The raw material of the invention is simple and easy to obtain, the reaction conditions are mild, and the operation is simple and convenient.

Description

technical field [0001] The invention relates to a method for preparing beta-haloether and beta-halohydrin catalyzed by peroxidase, and belongs to the field of biotechnology. Background technique [0002] Halogenated ether compounds are widely used. Several general anesthetics 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 anesthesia drugs, which has the advantages of low metabolic rate, low 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 oleum. Synthesis of sevoflurane. In this reaction, hydrogen fluoride is a poisonous gas with a pungent odor, which is expensive and causes environmental pollution, and oleum is a hazardous chemical, which has strong irritating and corrosive effects on human skin, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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