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Method for stereoselectively separating carprofen enantiomer through biological enzyme catalysis

A technology of stereoselectivity and enantiomers, applied in the direction of fermentation, etc., can solve the problems of optical purity and low yield of products separating chiral enantiomers, and achieve high stereoselectivity, high catalytic efficiency, and reaction conditions mild effect

Active Publication Date: 2017-11-07
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Aiming at the problems of low optical purity and low yield of chiral enantiomers separated by the general racemate resolution method, the present invention proposes a method for obtaining (S)-carprofen—using Candida antarctica Method for the synthesis of single enantiomer carprofen with high selectivity and high catalytic efficiency of lipase A to carprofen ester enantiomers

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 20 mmol of carprofen ester enantiomers and 5 mg of several commercial lipases to 1 mL of sodium dihydrogen phosphate buffer solution with a pH of 6; The reaction was heated for 16 h; and the progress of the reaction and the optical purity of the product were analyzed by high performance liquid chromatography. The results showed that when Candida antarctica lipase A was used as a catalyst, the substrate conversion rate was 18.25%, and the optical purity of the product was 92.12%.

Embodiment 2

[0022] Add 20 mmol of carprofen ester enantiomers and 10 mg of Candida antarctica lipase A to 1 mL of sodium dihydrogen phosphate buffer solution with a pH of 6; Heat the reaction at 80°C for 4 h; and analyze the progress of the reaction and the optical purity of the product by high performance liquid chromatography; at this time, the conversion rate of the substrate is 17.79%, and the optical purity of the product is 94.16%.

Embodiment 3

[0024] Add 20 mmol of carprofen ester enantiomer and 10 mg of Candida antarctica lipase A to 1 mL of sodium dihydrogen phosphate buffer solution with pH 6.5; in a 25 mL reaction tube at 600 rpm, 80 °C The reaction was heated for 4 h; and the reaction progress and the optical purity of the product were analyzed by high performance liquid chromatography; at this time, the conversion rate of the substrate was 20.07%, and the optical purity of the product was 96.72%.

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PUM

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Abstract

The invention introduces a novel chiral separation method for acquiring a carprofen single enantiomer, namely a method for synthesizing the carprofen single enantiomer by stereoselectively hydrolyzing a carprofen enantiomer through biological enzyme catalysis. According to the method, candida Antarctica lipase A is utilized for hydrolyzing the carprofen enantiomer and cyclodextrin in a high selectivity and high catalytic efficiency manner so as to solubilize the carprofen enantiomer, so that the hydrolysis reaction of the carprofen enantiomer in a phosphate buffer solution is accelerated; the conversion rate of a substrate and the optical purity of a product can respectively reach 48.00% and 96.24%, and the stereoselectivity E is more than 145; the problems of low optical purity and yield, environmental pollution and the like in a common separation technique are overcome, and the high conversion rate and the high selectivity of the hydrolysis of the carprofen enantiomer can be realized, so that the purposes that non-toxic, harmless and environment-friendly separation of a chiral compound, reaction conditions are mild, the operation is simple and convenient, the cost is low and the like are achieved.

Description

technical field [0001] The invention belongs to the biological preparation of chiral compounds, and relates to a method for synthesizing (S)-carprofen enantiomer by using Candida antarctica lipase A stereoselectively to catalyze the hydrolysis of carprofen ester enantiomer. Candida antarctica lipase A (abbreviated as lipase A) was used to hydrolyze racemic carprofen ester of the structure shown in (1) to synthesize (2) in a single configuration. [0002] [0003] (1) (2) 【Background technique】 [0004] Carprofen (Carprofen) is a lipophilic non-steroidal high-efficiency anti-inflammatory drug, because of its good anti-inflammatory effect and small side effects. It is mainly used for the treatment of animal joints. Compared with other non-steroidal anti-inflammatory drugs (NSAIDs), it has obvious effects and has less toxic effects on the gastrointestinal tract and kidneys. Because carprofen has good efficacy and high added value, it has been widely used in many countrie...

Claims

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Application Information

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IPC IPC(8): C12P41/00C12P17/10
CPCC12P17/10C12P41/005
Inventor 唐课文张盼良刘光勇许卫凤熊碧权刘宇
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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