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Method for synthesizing poly-(R)-5-methyl-epsilon-caprolactone through three-enzyme catalysis by using microchannel reaction device

A microchannel reaction and caprolactone technology, applied in biochemical equipment and methods, enzymology/microbiology devices, bioreactor/fermenter combinations, etc., can solve the problem of low optical purity of caprolactone compounds and restricted application Popularization, serious environmental pollution and other problems, to achieve the effect of good mass transfer and heat transfer, avoiding technical difficulties and high optical purity

Pending Publication Date: 2022-04-12
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the caprolactone compounds prepared by these methods have low optical purity, and have disadvantages such as explosives and serious environmental pollution, which seriously restrict their application and promotion in my country.

Method used

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  • Method for synthesizing poly-(R)-5-methyl-epsilon-caprolactone through three-enzyme catalysis by using microchannel reaction device
  • Method for synthesizing poly-(R)-5-methyl-epsilon-caprolactone through three-enzyme catalysis by using microchannel reaction device
  • Method for synthesizing poly-(R)-5-methyl-epsilon-caprolactone through three-enzyme catalysis by using microchannel reaction device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Put 1mL of NCR in the state of 0.1g wet cells / mL whole cells into a 10mL eggplant-shaped flask, dissolve 3-methyl-cyclohexen-1-one in dimethyl sulfoxide to make 1M, take 10μL and add In the reaction system, the substrate concentration is 10 mM. After reacting at 25° C. for 30 minutes, (R)-3-methylcyclohexanone is generated by GC monitoring, and the reaction conversion rate is greater than or equal to 99%, and the ee value is greater than or equal to 99%. 1 H NMR (400MHz, CDCl 3 )δ4.10(1H,dt,J)12,1.2Hz),4.00(1H,dd J)12,8Hz),2.65(1H,t,J)3Hz),2.61(1H,t,J)16Hz) ,1.94(1H,m),1.86(1H,m),1.67(1H,m),1.38(2H,m),0.98(3H,d,J)20Hz)ppm. 13 C NMR (100MHz, CDCl 3 )δ176.0,73.9,36.9,34.4,33.8,21.6,17.7ppm.HRMS(ESI):m / z calc.for C 7 h 12 O[M+Na] + :135.0780,found:135.0784.

Embodiment 2

[0047] Put 1mL of NCR in the state of 0.1g wet cells / mL whole cells in a 10mL eggplant-shaped flask, dissolve 3-methyl-cyclohexen-1-one in dimethyl sulfoxide to make 1M, take 15μL and add In the reaction system, the substrate concentration is 15 mM. After reacting at 25° C. for 30 minutes, (R)-3-methylcyclohexanone is generated by GC monitoring, and the reaction conversion rate is greater than or equal to 99%, and the ee value is greater than or equal to 99%. HRMS(ESI):m / z calc.for C 7 h 12 O[M+K] + :151.0520,found:151.0525.

Embodiment 3

[0049] Put 1mL of NCR in the state of 0.1g wet cells / mL whole cells in a 10mL eggplant-shaped flask, dissolve 3-methyl-cyclohexen-1-one in dimethyl sulfoxide to make 1M, take 20μL and add In the reaction system, the substrate concentration is 20 mM. After reacting at 25° C. for 30 minutes, (R)-3-methylcyclohexanone is generated by GC monitoring, and the reaction conversion rate is greater than or equal to 99%, and the ee value is greater than or equal to 99%. HRMS(ESI):m / z calc.for C 7 h 12 O[M+Na] + :135.0780,found:135.0787.

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Abstract

The invention provides a method for synthesizing poly-(R)-5-methyl-epsilon-caprolactone by utilizing a micro-channel reaction device through three-enzyme catalysis, which comprises the following steps: S1, taking 3-methyl-2-cyclohexene-1-ketone as a raw material, and utilizing alkene reductase and cyclohexanone monooxygenase as biocatalysts to obtain (R)-5-methyl-epsilon-caprolactone; s2, carrying out polymerization on the (R)-5-methyl-epsilon-caprolactone in the micro-channel reaction device by using Novozymes 435 lipase as a biocatalyst, so as to obtain poly-(R)-5-methyl-epsilon-caprolactone; wherein the number average molecular weight of the poly-(R)-5-methyl-epsilon-caprolactone is in a range of 7500 to 18550. The method has the advantages of mild reaction conditions, high catalytic efficiency, high product yield, high optical purity and the like.

Description

technical field [0001] The invention belongs to the technical field of preparation, and in particular relates to a method for synthesizing poly-(R)-5-methyl-ε-caprolactone by using a microchannel reaction device and catalyzing three enzymes. Background technique [0002] Polycaprolactone compounds are a class of materials with good biocompatibility, biodegradability, and drug permeability. Due to their good performance and shape memory properties, they are widely used in medicine and health, biomedical engineering, flame retardant materials, 3D There are potential applications in various fields such as printing technology. Caprolactone compound is a kind of precursor of polyester, and its synthesis method is mainly divided into chemical method and biological method. The industrially mature chemical method for preparing caprolactone compounds is mainly prepared by catalyzing the Baeyer-Villiger (B-V oxidation) reaction of cyclohexanone compounds such as oxidant peroxyacid an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/625C12M1/40C12M1/00
Inventor 郭凯王雨清胡玉静方正李振江
Owner NANJING UNIV OF TECH
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