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Method for preparing S type cyclopentenone by sol-gel embedding immobilized enzyme

A cyclopentenone, immobilized enzyme technology, applied in biochemical equipment and methods, microorganism-based methods, immobilized on/in organic carriers, etc., to achieve the effect of improving operational stability

Inactive Publication Date: 2009-04-29
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on the application of sol-gel immobilized lipase to the transesterification of allyl alcohol ketone or propargyl alcohol ketone

Method used

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  • Method for preparing S type cyclopentenone by sol-gel embedding immobilized enzyme
  • Method for preparing S type cyclopentenone by sol-gel embedding immobilized enzyme

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] 1) In a mixture of γ-methacryloxypropyltrimethoxysilane and methyl orthosilicate with a total volume of 1ml and a molar ratio of 1:3, add 0.5ml of deionized water, 30μl of 0.1mol / 1 hydrochloric acid solution, and stirred at 200rpm, 0°C for 30min to form a uniform sol;

[0015] 2) Add a buffer solution containing 0.005g lipase Arthrobacter sp. to the sol, the concentration of the buffer solution is 0.03M, pH7.0, and the dosage is 0.5ml; after stirring for 10min, continue stirring at 100rpm for 1h; at 4°C Standing and aging under the condition overnight, vacuum drying at 25°C for 7 days, grinding to obtain the embedded immobilized lipase;

[0016] 3) Add allyl alcohol ketone with a concentration of 0.1 mol / L, vinyl acetate with a concentration of 0.5 mol / L, and acetonitrile with a volume of 5 ml into a 10 ml Erlenmeyer flask with a stopper. Then add 25 mg of embedded immobilized lipase and react in a shaker with a rotational speed of 200 rpm at a reaction temperature of...

Embodiment 2

[0018] 1) In a mixture of γ-methacryloxypropyltrimethoxysilane and ethyl orthosilicate with a total volume of 1ml and a molar ratio of 3:1, add 0.5ml of deionized water, 30μl of 0.1mol / 1 sodium hydroxide solution, and stirred at 250rpm, 10°C for 30min to form a uniform sol;

[0019] 2) Add a buffer containing 0.02g lipase Arthrobacter sp. to the sol, the concentration of the buffer is 0.03M, pH9.0, and the dosage is 1ml; after stirring for 20min, continue stirring at 100rpm for 3h; Standing and aging overnight, vacuum-drying at 35°C for 10 days, grinding to obtain embedded immobilized lipase;

[0020] 3) In a 10ml Erlenmeyer flask with a stopper, add a concentration of 3mol / L propargyl alcohol ketone, a concentration of 10mol / L vinyl acetate, a volume of 10ml of toluene, add 25mg of embedded immobilized lipase at a speed of 250rpm The reaction is carried out in a shaking table; the reaction temperature is 50° C., the reaction is 8 hours, the conversion rate reaches 49%, and ...

Embodiment 3

[0022] 1) In a mixture of γ-methacryloxypropyltrimethoxysilane and methyl orthosilicate with a total volume of 1ml and a molar ratio of 1:1, add 0.5ml of deionized water, 30μl of 0.1mol / 1 hydrochloric acid solution, and stirred at 250rpm, 0°C for 30min to form a uniform sol;

[0023] 2) Add a buffer containing 0.01g of lipase Arthrobacter sp. to the sol, the concentration of the buffer is 0.03M, pH8.0, and the dosage is 0.5ml; after stirring for 10min, continue stirring for 1h at 100rpm; at 4°C Under the condition of standing and aging overnight, vacuum drying at 35°C for 7 days, and grinding to obtain embedded immobilized lipase 1#;

[0024] 3) In a 10ml Erlenmeyer flask with a stopper, add a concentration of 1mol / L of propargyl alcohol ketone, a concentration of 5mol / L of vinyl acetate, a volume of 5ml of acetonitrile, add 25mg of embedded immobilized lipase at a speed of 250rpm The reaction is carried out in a shaking table; the reaction temperature is 50° C., the reactio...

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Abstract

The invention discloses a method for preparing S-type cyclopentenone from a sol gel embedded immobilized enzyme. The method comprises the following steps: 1) using an organic silane reagent as a precursor to react with water under the catalysis of acid or alkali so as to generate a sol; 2) adding a buffer solution containing enzyme powder into the mixture, and mixing, keeping stand for aging, and drying the mixture to obtain the sol gel embedded immobilized enzyme; and 3) using the sol gel embedded immobilized enzyme as a catalyst to perform enantiomeric separation reaction with cyclopentenone in an organic phase so as to obtain the S-type cyclopentenone. The method is characterized in that the used lipase is Pseudomonas aeruginosa, Arthrobacter sp. and Acinetobacter sp.; the precursor is gamma-methacryloyl-oxypropyl-trimethoxysilane or alkyl-trimethoxysilane, or a mixture of the gamma-methacryloyl-oxypropyl-trimethoxysilane or the alkyl-trimethoxysilane and n-methyl silicate or ethyl orthosilicate; and the cyclopentenone is allyl alcohol ketone or propargyl alcohol ketone. The vitality, the stability, the enantioselectivity and the like of the immobilized enzyme related in the invention are significantly improved in the split reaction of the cyclopentenone.

Description

technical field [0001] The invention relates to a preparation method of chiral compounds, in particular to a method for preparing S-type cyclopentenone by embedding immobilized enzyme in sol-gel. Background technique [0002] Allyl alcohol ketone and propargyl alcohol ketone are important intermediates of pyrethroid insecticides. Pyrethroid is a new type of high-efficiency hygienic insecticide. There are eight optical enantiomers, among which the trans-chrysanthemum ester of S-type allyl alcohol ketone or S-type propargyl alcohol ketone has the strongest biological activity, so In order to reduce the application amount and avoid unnecessary environmental pollution, obtaining optically pure allyl alcohol ketone is a key step in the synthesis of highly active permethrin. Lipase is widely used in organic synthesis and chiral resolution of optical compounds due to its specific catalytic activity at the oil-water interface, mild reaction conditions, high catalytic stability, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12N11/04C12P41/00C12P7/38C12R1/385C12R1/06C12R1/01
Inventor 杨立荣杨光徐刚吴坚平
Owner ZHEJIANG UNIV
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