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Method for preparing (R)-phenyl glycol

A technology of phenylethylene glycol and styrene oxide, which is applied in the field of mung bean epoxide hydrolase catalyzed hydrolysis to prepare phenylethylene glycol, can solve the problem of non-enzymatic hydrolysis reaction of epoxy compounds, low reaction substrate concentration, Reduced ee value of the product and other issues, to achieve the effect of easy product, simple and easy control of the reaction process, and increased ee value

Active Publication Date: 2015-04-22
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

Studies have shown that the use of epoxide hydrolase derived from Rhodobacterales bacterium HTCC2654 and Botryosphaeria dothidea ZJUZQ007 can catalyze the hydrolysis of epoxides with high stereoselectivity, and the ee value of the product can reach 91%-99%, but the yield is lower than 43 %(WooJ.H., Kang J.H., Hwang Y.O., et al.J.Biosci.Bioeng., 2010, 109:539; Sheng Y.M., Wei C., Zhang Z.F., et al.Appl.Biochem.Biotechnol., 2011 , 164:125)
[0004] In recent years, mung bean epoxide hydrolase, which has a wide range of sources and low price, has been used to synthesize enantiomerically pure chiral ortho diols, showing great application potential, but the hydrolysis reaction is only carried out in the aqueous phase, because when When the reaction is carried out in the aqueous phase system, the epoxy compound is prone to non-enzymatic hydrolysis reaction, resulting in a decrease in the ee value of the product; in addition, the solubility of the epoxy compound in the aqueous phase is generally poor, and the concentration of the reaction substrate is biased. low, will also lead to low reaction efficiency

Method used

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  • Method for preparing (R)-phenyl glycol
  • Method for preparing (R)-phenyl glycol

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Embodiment 1

[0026] Add 1mL C to a 20mL Erlenmeyer flask with stopper 4 MIM·PF 6 and 6mL phosphate buffer (100mmol / L, pH 6.5) to form a biphasic system with a volume ratio of 1:6, then add 79.8μL epoxystyrene (100mmol / L) and 4.74U mung bean epoxide hydrolase Coarse enzyme powder is placed in a water bath shaker (220r / min) at 35°C for reaction. After reacting for 36 hours, the ionic liquid and phosphate buffer were separated by centrifugation, sodium chloride was added to the phosphate buffer to saturation, and then extracted with ethyl acetate, and the extract was rotary evaporated to remove ethyl acetate to obtain the product (R)-phenyl ethylene glycol. Product detection: two samples were taken from the buffer solution, and 2 times the volume of ethyl acetate (containing 7.7mmol / L p-chloroacetophenone) was added to one of them to extract the product for GC analysis of the ee value of the product; the other sample was used Methanol / water (30:70, v / v) was diluted 5 times, centrifuged (10...

Embodiment 2

[0028] Add 1mL C to a 20mL Erlenmeyer flask with stopper 4 MIM·PF 6 and 6mL phosphate buffer (100mmol / L, pH 6.5) to form a biphasic system with a volume ratio of 1:6, then add 15.96μL epoxystyrene (20mmol / L) and 4.74U mung bean epoxide hydrolase Coarse enzyme powder is placed in a water bath shaker (220r / min) at 35°C for reaction. After 12 h of reaction, (R)-phenylethylene glycol was obtained with an enantiomeric excess ee of 96.6% enantiomeric purity and a yield of 49.5%.

Embodiment 3

[0030] Add 1mL C to a 20mL Erlenmeyer flask with stopper 4 MIM·PF 6 and 6mL phosphate buffer (100mmol / L, pH 7.0) to form a biphasic system with a volume ratio of 1:6, then add 15.96μL epoxystyrene (20mmol / L) and 4.74U mung bean epoxide hydrolase Coarse enzyme powder is placed in a water bath shaker (220r / min) at 35°C for reaction. After 12 h of reaction, (R)-phenylethylene glycol was obtained with an enantiomeric excess ee of 96.3% enantiomeric purity and a yield of 49.2%.

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Abstract

The invention discloses a method for preparing (R)-phenyl glycol. The method comprises the following steps: (1) preparing a diphasic system of hydrophobic ionic liquid and phosphate buffer, and adding reaction substrate epoxy styrene into the diphasic system; (2) adding mung bean epoxide hydrolase into the above system, regulating the pH value of the system to 6.0-8.0, and carrying out enzyme catalytic hydrolysis reaction at the temperature of 20-45DEG C and the oscillation speed of 160-260r / min; and (3) carrying out ultrafiltration to remove suspended particles and enzyme in the reaction mixture, separating ionic liquid and phosphate buffer, and separating in the phosphate buffer to obtain the product (R)-phenyl glycol. The concentration of reaction substrate in the method is as high as 100mM, the enantiomeric purity of the obtained (R)-phenyl glycol product is above 90%ee, and the enantiomeric purity and the yield of the product are both improved.

Description

technical field [0001] The invention belongs to the technical field of biocatalytic asymmetric synthesis of chiral compounds, in particular to a method for preparing (R)-phenylethylene glycol by catalyzing hydrolysis of mung bean epoxide hydrolase in a hydrophobic ionic liquid medium. Background technique [0002] The optically active epoxy compounds obtained by stereoselective ring-opening hydrolysis of chiral epoxides and the corresponding vicinal diols are extremely important chiral intermediates in fine organic synthesis. After further transformation, white three There are many biologically active compounds such as alkenes, insect pheromones, steroids, and AIDS virus protease inhibitors, which have important application values ​​in the pharmaceutical and pesticide industries. [0003] The reaction conditions for the synthesis of optically active epoxy compounds and vicinal diols by traditional chemical methods are relatively harsh, and it is difficult to obtain the targe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P7/22
Inventor 娄文勇宗敏华陈文静吴虹
Owner SOUTH CHINA UNIV OF TECH
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