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Method for preparing (S)-benzoglycol by microorganism unsymmetrical split

A kind of phenylethylene glycol, microorganism technology, applied in biological field

Inactive Publication Date: 2008-11-12
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, the method for obtaining the product (S)-phenylethylene glycol by selectively oxidizing (R)-phenylethylene glycol in the racemic substrate by using the microorganisms of the genus Gluconobacter (Gluconobacter) has not yet been reported.

Method used

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  • Method for preparing (S)-benzoglycol by microorganism unsymmetrical split
  • Method for preparing (S)-benzoglycol by microorganism unsymmetrical split
  • Method for preparing (S)-benzoglycol by microorganism unsymmetrical split

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 , strain culture

[0034] Prepare seed medium and fermentation medium according to the following formulas:

[0035] DSM2003 strain seed medium: take 8.0g sorbitol, 2.0g yeast extract, 0.1g KH 2 PO 4 , 0.05g MgSO 4 ·7H 2 O, pH6.0, add distilled water to make 100ml culture medium.

[0036] DSM2003 strain fermentation medium: take 8.0g sorbitol, 2.0g yeast extract, 0.1g KH 2 PO 4 , 0.05g MgSO 4 ·7H 2 O, pH 6.0 was added to distilled water to make 100ml culture medium.

[0037] Take the DSM2003 strain of Gluconobacter oxydans (Gluconobacter oxydans), add it to the seed medium, and culture it with shaking at 200 rpm for 24 hours at 28°C to obtain the seed culture solution, and then add the seed culture solution to the fermentation culture at an inoculum size of 10%. medium, at 25-30°C, 100-300rpm, cultivated for 24 hours, and harvested the fermentation broth.

[0038] The fermentation broth was centrifuged to collect the bacterial cell precipitate, and t...

Embodiment 2

[0039] Example 2 , the influence of reaction time on preparation (S)-phenylethylene glycol

[0040] In the 40ml 0.1mol / L phosphate buffer solution that racemic phenylethylene glycol (substrate) concentration is 10g / L, add the wet thalline of the DSM2003 that 0.3g embodiment 1 obtains, carry out selective oxidation reaction, between reactor , adjust the pH to 5.5 intermittently, and the reaction temperature is 28°C.

[0041] As shown in Table 1, samples were taken at regular intervals, and the supernatant was collected after centrifugation of the sample, extracted with an equal volume of ether, and the organic phase was collected to detect (R)-phenylethylene glycol, (S)-phenylethylene glycol and (R, S)-phenylethylene glycol content, calculate the optical purity and the productive rate of (S)-phenylethylene glycol, the results are shown in Table 1.

[0042] Table 1, the influence of reaction time on preparation (S)-phenylethylene glycol

[0043] Reaction time

[0...

Embodiment 3

[0045] Example 3 , the influence of substrate concentration on the preparation of (S)-phenylethylene glycol

[0046] As shown in table 2, in the 10ml 0.1mol / L phosphate buffer solution of different racemic phenylethylene glycol (substrate) concentrations, add the wet thalline of the DSM2003 that a certain amount of embodiment 1 obtains, carry out selective oxidation reaction , the reaction maintained at pH 6.0, and the reaction temperature was 28°C.

[0047] Stop the reaction after 36 hours, centrifuge the reaction solution, collect the supernatant, extract with an equal volume of ether, collect the organic phase, and detect (R)-phenylethylene glycol, (S)-phenylethylene glycol and (R, S) -Phenylethylene glycol content, calculate the optical purity and productive rate of (S)-phenylethylene glycol, the results are shown in table 2.

[0048] Table 2, the influence of substrate concentration on preparation (S)-phenylethylene glycol

[0049] Substrate concentration

...

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Abstract

The invention provides a method for preparing (S)-styrolylalcohol by microorganism asymmetric resolution. The method uses Gluconobacter microorganisms to selectively oxidize (R)-styrolylalcohol in racemic styrolylalcohol, thereby obtaining the (S)-styrolylalcohol. When the method is used to prepare the (S)-styrolylalcohol, the optical purity can reach more than 99.9 percent (e. e.), and the yieldcan reach about 38 percent.

Description

technical field [0001] The invention belongs to the field of biotechnology, in particular, the invention relates to a method for preparing (S)-phenylethylene glycol by asymmetric resolution of microorganisms. Background technique [0002] (S)-Phenylethylene glycol is not only an indispensable chiral raw material in liquid crystal materials, but also can be used to convert and synthesize optically pure epoxy compounds, azide compounds and amino alcohols. important intermediates of materials. For example, (S)-phenylethylene glycol, as the precursor of chiral bisphosphine, plays an important role in the synthesis of rhodium ion complexes as catalysts for asymmetric hydrogenation to generate prochiral alkenes; in addition, (S)-benzene Ethylene glycol is also the starting chiral synthon for stereoselective polymers. Therefore, it is very meaningful to carry out research on the separation method of phenylethylene glycol. [0003] The chemical structures of (R, S)-phenylethylene...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/22C12P41/00C12N1/20C12R1/01
Inventor 魏东芝林金萍高琼
Owner EAST CHINA UNIV OF SCI & TECH
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