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Biological preparation method of (R)-1-(2-trifluoromethylphenyl)ethanol

A technology of trifluoromethyl phenyl and ethanol, which is applied in the field of biological preparation of -1-ethanol, can solve problems such as difficult degradation of metal compounds and environmental pollution, and achieve the effects of environmental friendliness, excellent catalytic efficiency and high conversion rate

Active Publication Date: 2018-03-02
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chemical catalysts are mostly used in the preparation of (R)-1-(2-trifluoromethylphenyl)ethanol by chemical methods. These catalysts contain metal compounds that are not easy to degrade and are easy to cause pollution to the environment

Method used

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  • Biological preparation method of (R)-1-(2-trifluoromethylphenyl)ethanol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Screening of microbial strains for catalytic reduction of 2,6-dichloro-3-fluorophenethyl alcohol

[0030] 1. Strain screening

[0031] Enrichment culture: Add 1g of fresh soil samples (collected from the campus of Zhejiang University of Technology (Hangzhou, Zhejiang)) into a 250mL shake flask containing 50mL enrichment medium, culture at 30°C and 200rpm for 5 days, and take 1mL for culture The culture medium was transferred to fresh enrichment medium, and the culture was continued for 5 days, and the enrichment was repeated twice. The enrichment medium consists of: (NH 4 ) 2 SO 4 2g / L, KH 2 PO 4 2g / L, NaCl 1g / L, MgSO 4 ·7H 2 O 0.5g / L, the compound of formula (II) (2g / L) is the only carbon source, the solvent is distilled water, pH6.5.

[0032] Plate primary screening: the enriched culture solution was diluted 10 with normal saline 4 -10 6 After doubling, it was spread on the plate to select medium, and cultured at 30°C for 2 days. Pick a single ...

Embodiment 2

[0050] Example 2: Acquisition of resting cell enzyme source for the preparation of (R)-1-(2-trifluoromethylphenyl)ethanol under shake flask culture conditions

[0051] (1) Preservation on slant: use an inoculation loop to pick Geotrichum candidum ZJPH1704 and inoculate it on the slant medium, culture at 30°C for 1-2 days, take it out and store it in a refrigerator at 4°C for later use. Slant medium composition (g / L): glucose 15, peptone 5, yeast extract 5, K 2 HPO 4 0.5, KH2 PO 4 0.5, MgSO 4 ·7H 2 O 0.5, NaCl 1, (NH 4 ) 2 SO 4 1. Agar 20, the solvent is distilled water, pH 7.0, sterilized at 121°C for 20min.

[0052] (2) Plate preservation: pick a ring of bacteria from the mature slant to the plate medium, culture at 30°C for 1-2 days, take it out and store it in a refrigerator at 4°C for later use. Plate medium composition (g / L): glucose 15, peptone 5, yeast extract 5, K 2 HPO 4 0.5, KH 2 PO 4 0.5, MgSO 4 ·7H 2 O 0.5, NaCl 1, (NH 4 ) 2 SO 4 1. Agar 20, th...

Embodiment 3

[0055] Example 3 The effect of auxiliary substrate types on the bioreduction of Geotrichum candidum ZJPH1704 to prepare (R)-1-(2-trifluoromethylphenyl)ethanol

[0056] The wet thallus of Geotrichum candidum ZJPH1704 obtained by the method of Example 2 is used as a biocatalyst. Take a 50mL Erlenmeyer flask, add 2g of wet thallus to be suspended in 10mL, pH 7.0 of 0.2M phosphate buffer, add a final concentration of 10mmol / L Material 2-trifluoromethyl acetophenone, add the auxiliary substrate of final concentration 100g / L respectively: maltose, lactose, sucrose, glycerol, glucose, methyl alcohol, ethanol, isopropanol, n-butanol (as shown in table 1 ), reacted at 30°C, 200rpm shaker for 48h. After the reaction, add an equal volume of ethyl acetate to the reaction solution to terminate the reaction and extract for 30 min, centrifuge at 8000 rpm and 4°C for 10 min, get the organic phase and filter it through a 0.45 μm microporous membrane, and then perform gas phase detection ( Fi...

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Abstract

The invention discloses a biological preparation method of (R)-1-(2-trifluoromethylphenyl)ethanol. The method comprises the following steps: taking a wet thallus obtained by carrying out fermentationculture on geotrichum candidum ZJPH1704 as a biological catalyst and taking 2-trifluoromethylacetophenone as a substrate; carrying out biological reduction reaction in a phosphoric acid buffering solution with the pH (Potential of Hydrogen) of 5.8 to 8.0 under the condition that the temperature is 25 DEG C to 40 DEG C and the speed is 200rpm; after the reaction is finished, carrying out separationand purification on a reaction solution to obtain the (R)-1-(2-trifluoromethylphenyl)ethanol. According to the method disclosed by the invention, when the concentration of the substrate is 10mmol / L,the yield of the product (R)-1-(2-trifluoromethylphenyl)ethanol is 92.31 percent and the e.e. value is greater than 99 percent; the product has better catalysis efficiency. Compared with a reported conversion strain, the stereoselectivity and the yield of converting the catalytic conversion substrate 2-trifluoromethylacetophenone of the strain into the product are relatively high.

Description

(1) Technical field [0001] The invention relates to a biological preparation method of (R)-1-(2-trifluoromethylphenyl)ethanol. (2) Background technology [0002] The chemical structural formula of GSK461364(Ⅲ) is: [0003] [0004] 5-[6-[(4-Methyl-1-piperazinyl)methyl]-1H-benzimidazol-1-yl]-3-[(1R)-1-[2-(trifluoromethyl )phenyl]ethoxy]-2-thiophene carboxamide (GSK461364, III) is a Plk1 kinase inhibitor. Plk1 kinase inhibitors are a new class of cancer therapeutic drugs with good application prospects, which have better selectivity, tolerance and Advantages of clinical application. [0005] [0006] Formula (IV) is 2-trifluoromethylacetophenone, formula (V-a) is (S)-1-(2-trifluoromethylphenyl) ethanol, and formula (V-b) is (R)-1-( 2-trifluoromethylphenyl)ethanol. [0007] (R)-1-(2-trifluoromethylphenyl)ethanol (V-b) is an important chiral intermediate for the synthesis of GSK461364. At present, there are two synthetic methods of (R)-1-(2-trifluoromethylphenyl)etha...

Claims

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Application Information

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IPC IPC(8): C12P7/22C12N1/14C12R1/645
CPCC12N1/14C12P7/22
Inventor 王普牛婷婷陈樱陈和洁
Owner ZHEJIANG UNIV OF TECH
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