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Synthetic method of chiral 1,3-dihydroxyl-1-aryl acetone compound

A technology of arylacetone and hydroxypyruvate, applied in the field of biocatalysis, can solve the problems of narrow transketolase and low activity

Active Publication Date: 2021-11-19
TIANJIN INST OF IND BIOTECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the substrate spectrum of transketolase is still relatively narrow, and the low activity is also the main factor limiting its development and application.
At present, there is no research report on the synthesis of dihydroxyketones from hydroxypyruvate catalyzed by pyruvate decarboxylase

Method used

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  • Synthetic method of chiral 1,3-dihydroxyl-1-aryl acetone compound
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  • Synthetic method of chiral 1,3-dihydroxyl-1-aryl acetone compound

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Experimental program
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Effect test

Embodiment 1

[0022] Embodiment 1: Construction and cultivation of genetically engineered bacteria

[0023]The specific construction and cultivation method of the genetically engineered bacteria producing pyruvate decarboxylase is as follows: the pyruvate decarboxylase nucleic acid sequence SEQ ID NO: 3 derived from Macrococcushajekii is gene-synthesized, constructed into a pET series vector, and placed in the host bacteria Escherichia coli for heterologous expression. Thaw the strains stored at -80°C, streak on the plate, and culture overnight in a constant temperature incubator at 37°C. Select a single colony on the plate and inoculate it into 20mL LB medium containing the corresponding antibiotic, cultivate it for about 12 hours as a seed solution, inoculate it into 700mL LB medium containing the corresponding antibiotic according to the inoculation amount of 1%, and inoculate it on a shaker at 37°C and 200rpm Grow to OD 600 =0.6-0.8, add IPTG with a final concentration of 0.1 mmol / L t...

Embodiment 2

[0025] Example 2: Pyruvate decarboxylase catalyzes benzaldehyde and hydroxypyruvate to prepare 1,3-dihydroxy-1-phenylacetone.

[0026] (1) 0.26g hydroxypyruvate (25mM), 0.01g ThDP (0.1mM), 3.00g pyruvate decarboxylase genetically engineered bacteria, 20mM benzaldehyde (dissolved in 20% DMSO) were added in 80mL water, and the pH of the reaction system was adjusted to 8.0, react at 25°C for 24h. After the reaction, the protein was removed by centrifugation, the supernatant was extracted with ethyl acetate, and the extraction was confirmed by thin-layer chromatography. The organic solvent was removed by rotary evaporation to obtain the crude product, the substrate conversion rate and product yield were detected by gas phase, and the ratio of product and by-product isomers was detected by liquid phase HPLC. The test results are: the pyruvate decarboxylase catalyzes the R-configuration product, the ee value is >99%, the benzaldehyde substrate conversion rate is 61%, and the ratio ...

Embodiment 3

[0032] Example 3: Preparation of 1,3-dihydroxy-1-arylacetone by genetically engineered bacteria with pyruvate decarboxylase and D-amino acid oxidase.

[0033] With 2.00g D-amino acid oxidase genetically engineered bacteria, 3.00g pyruvate decarboxylase genetically engineered bacteria, 1.05g D-Serine (100mM), 0.02g MgCl 2 ·6H 2 Add O (1mM), 0.01g ThDP (0.1mM), 60mg catalase (15KU) into 80mL water, adjust the pH of the reaction system to 7.0, incubate at 25°C, 200rpm for 1h, then add 20mM benzaldehyde (dissolved in 20% DMSO) to react for 24h . After the reaction, the protein was removed by centrifugation, the supernatant was extracted with ethyl acetate, and the extraction was confirmed by thin-layer chromatography. The organic solvent was removed by rotary evaporation to obtain the crude product, the substrate conversion rate and product yield were detected by gas phase, and the ratio of product and by-product isomers was detected by liquid phase HPLC. The test results are: ...

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Abstract

The invention discloses a method for generating optically homochiral 1,3-dihydroxy-1-substituted arylacetone by catalyzing the reaction of hydroxypyruvic acid and benzaldehyde with different substituents by a biocatalyst. In order to obtain hydroxypyruvate cheaply, it is obtained by converting D-serine with D-amino acid oxidase, without separation, and the method has the remarkable characteristics of mild reaction conditions, good stereoselectivity, and no pollution.

Description

technical field [0001] The invention belongs to the field of biocatalysis, and relates to the use of biocatalyst pyruvate decarboxylase to catalyze the reaction of hydroxypyruvate and benzaldehyde with different substituents to generate optically pure chiral 1,3-dihydroxy-1-aryl acetone compound. Background technique [0002] 1,3-Dihydroxy ketones are important intermediates in the synthesis of many substances. Chiral amino alcohols, rare sugars and steroids can be obtained by using hydroxy ketones. They are used in functional foods, medicines, drugs and synthetic chemistry. It has great application potential. [0003] Currently, the methods for synthesizing 1,3-dihydroxy-1-arylacetone are mainly divided into two categories—chemical method and enzymatic method. According to literature reports, Mark E.B.Smith et al. used 3-(4-morpholino)-propanesulfonic acid as a solvent to promote the formation of a C-C bond between the acceptor aldehyde and the donor aldehyde, and achieved...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12N9/88C12P7/26
CPCC12N9/88C12P7/26C12Y401/01001
Inventor 姚培圆李宇崔云凤陈曦冯进辉吴洽庆朱敦明马延和
Owner TIANJIN INST OF IND BIOTECH CHINESE ACADEMY OF SCI