Method for degrading dibenzothiophene by artificial nicotinamide cofactor mediated enzyme method

A dibenzothiophene and nicotinamide technology, applied in the petroleum industry, hydrocarbon oil treatment, fermentation, etc., can solve the problems of low efficiency, heavy pollution, easy decoupling, etc., and achieve the effect of reducing costs and having a wide range of applications

Active Publication Date: 2021-11-05
ZHENGZHOU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Enzymatic methods generally use one or more enzymes, and the efficiency of enzyme cascade reactions is low, and decoupling is prone to occur
Chemical methods require organic noble metal complexes as catalysts, which are costly and polluting
The electrochemical method is easy to cause enzyme inactivation, and the photochemical method is limited by the lack of efficient photocatalysts, and the efficiency is low

Method used

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  • Method for degrading dibenzothiophene by artificial nicotinamide cofactor mediated enzyme method
  • Method for degrading dibenzothiophene by artificial nicotinamide cofactor mediated enzyme method
  • Method for degrading dibenzothiophene by artificial nicotinamide cofactor mediated enzyme method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1 takes figure 1 Reduced cofactors were synthesized in the manner indicated

[0041] (1) Synthesis of oxidized cofactors

[0042]Add nicotinamide (10mmol) in 80mL acetonitrile solution, then add benzyl bromide (12mmol), 1-bromobutane (12mmol), 1-bromooctane (12mmol), ethyl 4-bromomethylbenzoate ( 12mmol), 4-methoxybenzyl bromide (12mmol), the reaction temperature was 80°C, heated and stirred under reflux for about 12h, during the reaction, a white precipitate was precipitated. After the reaction was completed, the crude product was obtained by filtration, washed with ethyl acetate (15mL×3), and dried in vacuo. The yields were as follows:

[0043] 1a (1-benzyl-3-carbamoylpyridin-1-ium salt): 94%,

[0044] 3a (1-butyl-3-carbamoylpyridin-1-ium salt): 91%,

[0045] 5a (1-octyl-3-carbamoylpyridin-1-ium salt): 92%,

[0046] 6a (3-carbamoyl-1-(4-ethoxy-4-oxobutyl)pyridin-1-ium salt): 45%.

[0047] Add 5-methyl nicotinamide (10mmol) in 80mL acetonitrile solution,...

Embodiment 3

[0065] 50 mM 1 mL pH 7.5 Tris-HCl buffer containing 1 mM dibenzothiophene, 10 mM NADH or mNADHs (1b-8b), 10 μM FMN, 3 U DszC enzyme, 1 U DszD enzyme, 50 U catalase. 37°C, 200rpm, the reaction was carried out in a closed 1.5mL centrifuge tube, respectively take 200μL of the reaction solution for 2h, 4h, 8h, 12h, and 24h, add 3×200μL ethyl acetate to extract, ultrasonically mix, and centrifuge at 10000rpm for 2min, take The organic phase was detected by liquid phase, and the conversion rate (%) is shown in Table 1.

[0066] Table 1

[0067] time (h) NADH 1b 2b 3b 4b 5b 6b 7b 8b 2 57.23 17.93 20.79 21.53 22.11 22.78 15.03 55.98 59.87 4 68.36 21.65 25.81 39.82 40.51 38.98 28.99 84.76 63.77 8 99.28 43.78 50.70 57.58 66.39 57.22 39.73 93.92 82.10 12 99.41 76.93 89.23 96.23 94.58 81.11 54.78 97.90 96.88 24 100.0 89.14 92.54 99.69 98.65 89.32 67.80 98.93 100.0

Embodiment 4

[0069] 50 mM 1 mL pH 7.5 Tris-HCl buffer containing 1 mM dibenzothiophene, 2-30 mM mNADHs (3b, 4b, 7b, 8b), 10 μM FMN, 3 U DszC enzyme, 50 U catalase. 37°C, 200rpm, the reaction was carried out in a closed 1.5mL centrifuge tube, after 12h, take 200μL of each reaction solution, add 3×200μL ethyl acetate for extraction, ultrasonically mix, and centrifuge at 10000rpm for 2min, take the organic phase for liquid phase detection, the conversion rate (%)As shown in table 2.

[0070] Table 2

[0071] Equivalent (mM) 3b 4b 7b 8b 2 34.55 44.14 42.55 47.93 5 74.55 79.14 71.78 77.93 8 94.84 97.54 97.21 90.69 10 90.43 94.65 96.00 96.93 15 90.28 92.58 92.33 91.92 20 86.63 90.19 72.90 83.16 25 88.21 89.25 74.12 84.09 30 70.19 69.21 70.11 65.45

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Abstract

The invention discloses a method for degrading dibenzothiophene by an artificial nicotinamide cofactor mediated enzyme method, which comprises the following step: carrying out catalytic reaction on dibenzothiophene under the action of dibenzothiophene monooxygenase, flavin mononucleotide, an artificial nicotinamide cofactor and catalase to generate dibenzothiophene sulfone. According to the technical scheme provided by the invention, expensive natural cofactors can be prevented from being used for catalyzing the reaction, and cheap nicotinamide-like cofactors which are easy to be synthesized are used for assisting the enzyme catalysis reaction, so that the cost is reduced; compared with a natural cofactor, the artificial nicotinamide cofactor is more stable and has wide application range; the hydrogen supply capacity of the artificial cofactor 7b is superior to that of a natural cofactor, and the conversion rate of the catalytic reaction can reach 90% or above after 4 h.

Description

technical field [0001] The invention relates to the field of utilization synthesis, in particular to a method for enzymatically degrading dibenzothiophene mediated by artificial nicotinamide cofactor. Background technique [0002] The average content of sulfur in crude oil is between 0.05% and 5%, and the content in heavy oil can even be as high as 14%, which is the third largest element after C and H. More than 70% of the sulfur in crude oil exists in the form of dibenzothiophene and its derivatives, and these compounds can exist stably in the environment for more than three years. With fuel oil spills, mutagenic dibenzothiophenes are released into the environment, which has a great impact on the organisms in the ecosystem. Biological desulfurization has been paid attention to because of its low cost, mild conditions, environmental protection, and good removal effect on dibenzothiophene and other compounds that are difficult to remove by traditional hydrodesulfurization. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/00C10G32/00
CPCC12P17/00C10G32/00C10G2300/202
Inventor 应汉杰齐思雨谭卓涛欧阳平凯朱晨杰庄伟许敬亮王志刘金乐
Owner ZHENGZHOU UNIV
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