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Synthesis method of optically active aryl vicinal diol under catalysis of whole yeast cells

A technology of aryl vicinal diol and optical activity, which is applied in the field of preparation of novel optically active aryl vicinal diol, and achieves the effect of high application value

Inactive Publication Date: 2011-10-05
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation of chiral aryl glycols by asymmetric reduction of α-hydroxyaromatic ketones has not been reported.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Example 1: Add 0.1 mol / L, 100 mL of phosphate buffer solution of pH=6.2 and 15 g of yeast cells in an Erlenmeyer flask, shake (120 r / min) in a water bath constant temperature oscillator for 0.5 h at 32 ° C, Activate the yeast cells, then add 0.70g (7g / L) α-hydroxyacetophenone, shake the reaction at the same temperature for 36h. After the reaction, 100mL of ethyl acetate was added to the reaction solution, centrifuged after oscillating extraction, and the extract was separated. After the extract was concentrated, it was detected by a high-performance liquid chromatograph equipped with a Chiralcel OB-H chiral column. The conversion of α-hydroxyacetophenone and the enantiomeric excess of the product R-1,2-phenylethylene glycol were 83.2% and 97.0%, respectively. Finally, it was separated by column chromatography, petroleum ether / ethyl acetate=4:1 (V / V) was used as the eluent, and 0.46 g of R-1,2-phenylethylene glycol was obtained.

Embodiment 2

[0014] Example 2: Add 0.1 mol / L, 100 mL of phosphate buffer solution of pH=7.0 and 17 g of yeast cells in an Erlenmeyer flask, shake (120 r / min) in a water bath constant temperature oscillator for 0.5 h at 24 ° C, Activate the yeast cells, then add 0.50g (5.0g / L) α-hydroxy-p-methylacetophenone, and shake the reaction at the same temperature for 32h. After the reaction, 100mL of ethyl acetate was added to the reaction solution, centrifuged after oscillating extraction, and the extract was separated. After the extract was concentrated, it was detected by a high-performance liquid chromatograph equipped with a Chiralcel OB-H chiral column. The conversion of α-hydroxy-p-methylacetophenone and the enantiomeric excess of the product R-4'-methyl-1,2-phenylethylene glycol were 97.6% and 99.7%, respectively. Finally, it was separated by column chromatography, petroleum ether / ethyl acetate=4:1 (V / V) was used as the eluent, and 0.39 g of R-4'-methyl-1,2-phenylethylene glycol was obtained...

Embodiment 3

[0015] Example 3: Add 0.1 mol / L, 100 mL of phosphate buffer solution of pH=7.8 and 15 g of yeast cells in an Erlenmeyer flask, shake (120 r / min) in a water bath constant temperature oscillator for 0.5 h at 30 ° C, Activate the yeast cells, then add 1.5g (15g / L) α-hydroxy p-methoxyacetophenone, and shake the reaction at the same temperature for 36h. After the reaction, 100mL of ethyl acetate was added to the reaction solution, centrifuged after oscillating extraction, and the extract was separated. After the extract was concentrated, it was detected by a high-performance liquid chromatograph equipped with a Chiralcel OB-H chiral column. The conversion of α-hydroxy-p-methoxyacetophenone and the enantiomeric excess of the product R-4'-methoxy-1,2-phenylethylene glycol were 72.4% and 92.2%, respectively. Finally, it was separated by column chromatography, petroleum ether / ethyl acetate=4:1 (V / V) was used as the eluent, and 0.86 g of R-4'-methoxy-1,2-phenylethylene glycol was obtain...

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PUM

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Abstract

The invention relates to a preparation method of an optically active aryl vicinal diol by reducing an alpha-hydroxy aromatic ketone under catalysis of whole yeast cells, belonging to the technical field of optically active alcohol preparation utilizing a biological catalysis method. According to the invention, the whole yeast cells are used as a biocatalyst to catalyze the asymmetric reduction of the alpha-hydroxy aromatic ketone, so as to obtain high substrate conversion rate and high enantiomeric excess value of a product. Based on the invention, when the substrate concentration is 5.0-15 g / L, different conditions of whole yeast cell catalyst systems are selected according to the different substrates, thus the conversion rate of the substrate (alpha-hydroxy aryl ketone) reaches 72.4-98.4% and the enantiomeric excess value of the product (optically active aryl vicinal diol) reaches 92.2-99.7%, and the preparation has high application value.

Description

technical field [0001] The invention relates to the technical field of preparing optically active alcohols by a biocatalytic method, in particular to a preparation method of a novel optically active aryl vicinal diol. Background technique [0002] In addition to two hydroxyl groups, the optically active aryl o-diol molecule also has an aromatic ring in the molecule, which can undergo a series of functional group transformations, and properly modify or transform its structure. It can be used as the lead compound of some drugs, some Optically active aryl vicinal diol itself has certain biological activity. As an ideal chiral synthesis building block, optically active aryl vicinal diol is an important intermediate of many optically pure drugs. , materials and other fine chemical fields also have a wide range of application value. Therefore, it is of great significance to study and explore the synthesis methods of optically active aryl vicinal diols. [0003] The use of asymme...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/22
Inventor 刘湘王亿陈海波
Owner JIANGNAN UNIV
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