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Method for catalytic synthesis of (R)-1-[3, 5-bis (trifluoromethyl)] phenethyl alcohol through light-enzyme system

A technology of trifluoromethyl and phenethyl alcohol is applied in the field of photoenzyme system catalyzed synthesis of -1-[3,5-di]phenylethyl alcohol, which can solve the problems of high separation cost and limited enzyme stability.

Active Publication Date: 2021-09-14
HANGZHOU NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Enzyme-catalyzed regeneration of NADH (such as alcohol dehydrogenase and formate dehydrogenase (FDH)) has been established in industrial biocatalysis, however, this process usually requires the regeneration of the enzyme and the corresponding substrate, which is limited by the limited enzyme stability and high cost of separation

Method used

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  • Method for catalytic synthesis of (R)-1-[3, 5-bis (trifluoromethyl)] phenethyl alcohol through light-enzyme system
  • Method for catalytic synthesis of (R)-1-[3, 5-bis (trifluoromethyl)] phenethyl alcohol through light-enzyme system
  • Method for catalytic synthesis of (R)-1-[3, 5-bis (trifluoromethyl)] phenethyl alcohol through light-enzyme system

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Embodiment approach

[0037] The present invention is further analyzed below in conjunction with specific examples. It should be understood that the following examples are only used to illustrate the present invention but not to limit the protection scope of the present invention.

[0038] Raw material TiO used in the present invention 2 The nanopowder was purchased from Shanghai Macklin Biochemical Technology Co., Ltd.; the raw material rhodium trichloride trihydrate was purchased from Beijing Huawei Ruike Chemical Co., Ltd.; other raw materials of the present invention were purchased from the market unless otherwise specified.

Embodiment 1

[0040] Preparation of TiO 2 nanotube

[0041] 1g TiO 2 The nanopowder was dispersed in 100ml of 10M NaOH and stirred in a beaker for 30min; then the mixture was transferred to a Teflon-lined stainless steel autoclave at 140 °C for 18h; after the autoclave was naturally cooled to room temperature, The resulting precipitate was recovered by filtration and washed with distilled water and 0.1M HCl solution for 6 hours; subsequently, the solution was washed several times until the pH value was 7; the product was dried at 80 °C for 24 h, and then calcined in air at 400 °C for 2 h, TiO can be obtained 2 nanotube.

[0042] Prepared TiO 2 The XPS spectrum, SEM spectrum, TEM spectrum and EDS spectrum of nanotubes are as follows: figure 2 shown. From figure 2 It can be seen that the rhodium metal ligands were successfully adsorbed on the titanium dioxide nanotubes, and they were also successfully attached to the surface of the enzyme aggregates to form a composite catalytic mate...

Embodiment 2

[0054] 100mM PBS buffer (pH=7.0), 1mM NADP + , 1mM Cp*Rh(bpy) aqueous solution and 250μM TiO 2 Nanotubes, the final concentration is 32mg L -1 Enzyme protein, 50mM substrate 3,5-bis(trifluoromethyl)acetophenone, the total volume is 5ml, and the wavelength of xenon lamp 420nm is apart from the reactor 15 centimeters and reacts under light for 24h, the TiO 2 The nanotubes and enzyme protein are recycled, and the cycle is 12 hours once. After 5 cycles, the conversion rate of (R)-1-[3,5-bis(trifluoromethyl)]phenylethanol is basically unchanged by HPLC detection.

[0055] The (R)-1-[3,5-bis(trifluoromethyl)]phenylethanol provided by TCI (Tokyo Chemical Industry Co., Ltd.) and the product prepared by the method of the present invention are analyzed by HPLC, and the retention times of the two are consistent , to determine the structure of the product.

[0056] The inventive method is low in cost, uses TiO 2 The nanotube photolyzes water to supply hydrogen. The enzyme used is a cr...

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Abstract

The invention relates to a method for catalytic synthesis of (R)-1-[3, 5-bis (trifluoromethyl)] phenethyl alcohol by a light-enzyme system, which is characterized in that NADPH is catalytically regenerated by combining a TiO2 nanotube with [Cp*Rh(bpy)(H2O)]<2+>, and the generated NADPH is used for catalytic synthesis of (R)-1-[3, 5-bis (trifluoromethyl)] phenethyl alcohol. The method provided by the invention is low in cost, the TiO2 nanotube is used for supplying hydrogen through photocatalytic water splitting, the used enzyme is a cross-linked enzyme aggregation, which is insoluble in an organic solvent and can be recycled for multiple times, and the method has the advantages of high yield, safe, reliable, less environmental pollution and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of NADPH regeneration and the technical field of anti-tumor antiemetic drug synthesis, in particular to a photoenzyme system catalytic synthesis of (R)-1-[3,5-bis(trifluoromethyl)] The phenethyl alcohol method. Background technique [0002] (R)-1-[3,5-bis(trifluoromethyl)]phenylethanol (structural formula shown in B), is an important chirality of the key precursor for the synthesis of aprepitant (structural formula shown in A) intermediate. Obtained by direct reduction of 3,5-bis(trifluoromethyl)acetophenone (3,5-Bis(trifluoromethyl)acetophenone). Among them, optically active secondary alcohols are important components of many bioactive compounds in the pharmaceutical industry. In industrial production, asymmetric hydrogenation (AH, Asymmetric hydrogenation) of prochiral ketones is a practical and simple method to obtain enantiomerically pure secondary alcohols. [0003] [0004] Based on the previous...

Claims

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Application Information

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IPC IPC(8): C12P7/22B01J31/22B01J31/38C07H19/207C07H1/00
CPCC12P7/22B01J31/2295B01J31/38C07H19/207C07H1/00B01J2531/822
Inventor 谢恬王安明高鹏尹友程
Owner HANGZHOU NORMAL UNIVERSITY
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