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Streptomycete and application thereof in reduction of aromatic ketone

A technology of streptomyces and aromatic ketones, applied in the application of substituted fluorenone, streptomyces and its application in the field of reducing macrocyclic rigid aromatic ketones, can solve the problem of low yield and stereoselectivity, harsh chemical method conditions, and difficult aromatic ketones. Reduction and other problems, to achieve the effect of high stereoselectivity, less environmental pollution, and efficient reduction

Inactive Publication Date: 2009-04-29
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The object of the present invention is to aim at the characteristics of aromatic ketones, especially rigid macrocyclic aromatic ketones, which are difficult to reduce, and the chemical method conditions are harsh, difficult to control, low yield and stereoselectivity, and environmental pollution. Through scientific methods, screening, domestication and efficient reduction Aromatic ketone strains to solve the problems of chemical synthesis and industrial preparation of aromatic alcohols and optically active aromatic alcohols, and at the same time solve problems such as environmental pollution

Method used

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  • Streptomycete and application thereof in reduction of aromatic ketone
  • Streptomycete and application thereof in reduction of aromatic ketone
  • Streptomycete and application thereof in reduction of aromatic ketone

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Effect test

Embodiment 1

[0019] The steps of screening and domesticating Streptomyces are as follows:

[0020] Sampling was taken from the soil in the suburbs of Shanghai, and used as a source of bacteria for screening and domestication. Add a small amount of soil samples into the liquid large screening medium for shaker culture at a temperature of 28°C and a rotation speed of 170rpm; the formula of the liquid large screening medium is: 10g of soluble starch, 20g of glucose, 25g of soybean powder, 4g of yeast powder, and beef extract 1g, NaCl 2g, K 2 HPO 4 0.05g, 1L of water, pH 7.0-7.2. When the culture medium becomes turbid, carry out transfer and dilute the cultivation in separate bottles, and then coat the solid screening plate, put the solid plate into the light incubator for cultivation, and culture at 30°C for 4-5 days to pick a single colony. The solid screening plate formula is: 5g soluble starch, 5g glucose, 1g peptone, 1g yeast powder, 1g beef extract, 15g agar, 1L water, pH 7.0-7.2. T...

Embodiment 2

[0022] The optimum growth temperature of Streptomyces strains is 20-37°C, and the optimum growth pH is 6-8. On the large screening solid medium, the colonies are cocoon white or off-white, with a flat surface, well-developed hyphae, many branches, no septa, and a rod shape. It can grow well on most media, and the aerial hyphae and basal hyphae are mainly white or gray.

[0023] Amplification of 16S rDNA from Streptomyces:

[0024] By amplifying the 16S rDNA of the strain, a 16S rDNA sequence with a length of 1424bp was obtained. PCR primers use 16SrDNA amplification universal primers, 27f (5'-GAGTTTGATC(AC)TGGCTCAG-3') and 1492r

[0025] (5'-TACGG(CT)TACCTTGTTACGACTT-3'). The amplification reaction was carried out with a PCR machine. The reaction system is: TaKaRa PCR

[0026] 10×Buffer, 5μl; MgCl 2(25mM), 4μl; dNTP Mixture (2.5mM each), 4μl; primer 8f (20μm), 0.25μl; primer 1492r (20μm), 0.25μl; template DNA, 1μl; TaKaRa Taq (5U / μl), 0.25μl; Ultrapure water, up to 50μl...

Embodiment 3

[0036] The application steps of Streptomyces in the biocatalytic reduction of aromatic ketones are as follows:

[0037] (1) Streptomyces is placed in Tris-HCl buffer solution with a pH of 7.0-8.0 to make the cell concentration 50g (wet weight) / L, add aromatic ketone 2-substituted (fluorine, chlorine, bromine, iodine, formazan base) fluorenone, the concentration is 0.5mmol / l, placed in a shaker with a rotating speed of 200rpm and a temperature of 30°C for 12h;

[0038] (2) monitor the process of reaction with HPLC;

[0039] (3) After the reaction is completed, add an equal volume of ethyl acetate to extract the organic compound, remove water and some impurities through anhydrous magnesium sulfate column, concentrate under reduced pressure at 40°C, and separate to obtain a solid organic compound—aromatic alcohol substituted fluorenol .

[0040] (4) The pure aromatic alcohol compound-substituted fluorenol was obtained by silica gel column chromatography, identified by NMR and m...

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Abstract

The invention relates to the field of biocatalysis, and in particular relates to a streptomyces (Streptomyces sp.DUT003 with the preserving number of CGMCC2518) and application thereof in the reduction of rigid macrocyclic aromatic ketone such as substituted fluorenone. With the streptomyces, aromatic ketone, in particular the rigid macrocyclic aromatic ketone such as the substituted fluorenone can be reduced with high efficiency; products are aromatic alcohol and the aromatic alcohol with optical activity, the problems of synthesizing the aromatic alcohol and the aromatic alcohol with optical activity chemically and industrially are solved, the conversion rate can reach between 89 and 98 percent, the products have high stereoselectivity, and the ee value is between 83 and 100 percent. The streptomyces has the advantages of easy culture, mild reduction and reaction condition, simple operation steps, less environmental pollution, and good prospect of industrial application and development.

Description

technical field [0001] The invention relates to the field of biocatalysis, in particular to a streptomycete and its application in reducing macrocyclic rigid aromatic ketones, such as substituted fluorenones. technical background [0002] Aromatic alcohols or optically active aromatic alcohols are important structural units of many pharmaceutical intermediates, catalysts, analytical reagents, food additives, and advanced photoconductive materials. At present, it is mainly obtained chemically through the reduction of aromatic ketones. However, its synthetic method has problems such as cumbersome steps, low yield, high cost, and serious environmental pollution in chemistry. The reason is that the rigid structure of aromatic ketones creates high steric hindrance, which prevents the access of the catalyst. Especially, the reduction or stereoselective reduction of some rigid macrocyclic aromatic ketones such as substituted fluorenones is still a challenging issue in organic syn...

Claims

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Application Information

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IPC IPC(8): C12N1/20C12P7/22C12R1/465
Inventor 杨青谢波杨君陶黎明钱旭红
Owner DALIAN UNIV OF TECH
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