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Method for preparing (S)-4-decanol through biological catalysis

A technology of biocatalysis and decanol, which is applied in the direction of fermentation, etc., can solve problems such as the difficulty in obtaining chiral products with optical purity, the difficulty in achieving large-scale preparation of chiral purity, and the complex process conditions of the preparation method, achieving high yield and simple operation Ease of operation and good selectivity

Inactive Publication Date: 2019-03-19
SHANGHAI SYNTHEALL PHARM CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The technical problem to be solved by the present invention is to provide a preparation method of (S)-4-decanol with high yield and high chiral purity, which mainly solves the problem that the existing preparation method has complex process conditions and is difficult to obtain chiral products with high optical purity. , it is difficult to realize the technical problem of large-scale preparation of (S)-4-decanol with high chiral purity

Method used

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  • Method for preparing (S)-4-decanol through biological catalysis
  • Method for preparing (S)-4-decanol through biological catalysis
  • Method for preparing (S)-4-decanol through biological catalysis

Examples

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Effect test

Embodiment 1

[0035] In a 50mL glass jacketed reaction flask, add 20mL water, 0.212g KH 2 PO 4 and 0.557g K 2 HPO 4 , stir until the solid dissolves; add potassium hydroxide to adjust the pH value to 6.2-7.5; add 3g glucose, 1g ketoreductase (commercial reagent, purchased from Hequan Pharmaceutical, reagent number R308055), 0.02g NADP to the reaction solution and 0.2g GDH, after stirring, add 2g 4-decanone; adjust and control the temperature of the reaction solution to 25°C, pH 7.0, and continue to stir for 24 hours.

[0036]The reaction solution was extracted with 16 mL of methyl tert-butyl ether, the organic phase was collected, filtered by adding a small amount of anhydrous sodium sulfate to remove water, and concentrated by distillation under reduced pressure at 30°C. The obtained light yellow liquid is the product (S)-4-decanol, the crude yield is 92.7%, the conversion rate is 99.4% and the enantiomeric excess value is 97.6% according to the analysis by high performance gas chromato...

Embodiment 2

[0040] In a 50mL glass jacketed reaction flask, add 20mL water, 0.212g KH 2 PO 4 and 0.557g K 2 HPO 4 , stir until the solid dissolves; add potassium hydroxide to adjust the pH value to 6.2-7.5; add 2g glucose, 0.02g ketoreductase (commercial reagent, purchased from Hequan Pharmaceutical, reagent number R130709), 0.02g to the reaction solution NADP and 0.1g GDH, after stirring, add 1g of 4-decanone; adjust and control the temperature of the reaction solution to 25°C, pH 7.0, and continue to stir for 24 hours.

[0041] The reaction solution was extracted with 16 mL of methyl tert-butyl ether, the organic phase was collected, filtered by adding a small amount of anhydrous sodium sulfate to remove water, and concentrated by distillation under reduced pressure at 30°C. The obtained pale yellow liquid is the product (S)-4-decanol, the crude yield is 94.5%, and the conversion rate is 100% and the enantiomeric excess value is 100% through high performance gas chromatography analys...

Embodiment 3

[0044] In a 50mL glass jacketed reaction flask, add 20mL water, 0.212g KH 2 PO 4 and 0.557g K 2 HPO 4 , stir until the solid dissolves; add potassium hydroxide to adjust the pH value to 7.5; add 3g isopropanol, 1g ketoreductase (commercial reagent, purchased from Hequan Pharmaceutical, reagent number R130709) and 0.02g NAD to the reaction solution After stirring, add 2g of 4-decanone; adjust and control the temperature of the reaction solution to 25°C, pH 7.0, and continue stirring for 24 hours.

[0045] The reaction solution was extracted with 16 mL of methyl tert-butyl ether, the organic phase was collected, filtered by adding a small amount of anhydrous sodium sulfate to remove water, and concentrated by distillation under reduced pressure at 30°C. The obtained light yellow liquid is the product (S)-4-decanol, the crude yield is 96.2%, and the conversion rate is 100% and the enantiomeric excess value is 100% through high performance gas chromatography analysis. Analytic...

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Abstract

The invention discloses a method for preparing (S)-4-decanol through biological catalysis. The method comprises the step of preparing (S)-4-decanol from 4-decanone through enzymic catalytic reaction in the presence of a hydrogen source and coenzyme, wherein enzyme adopted in the enzymic catalytic reaction is selected from at least one of ketone reductase, aldehyde ketone reductase, carbonyl reductase or alcohol dehydrogenase, the pH value of the enzymic catalytic reaction is 6-8, the hydrogen source is selected from isopropanol or glucose or a mixture of isopropanol and glucose, and the coenzyme is selected from at least one of NAD, NADH, NADP or NADPH. According to the preparation method, an (S)-4-decanol product with a high optical purity can be acquired in a high conversion rate manner,and a chiral product, namely (S)-4-decanol with a high chemical purity and a high optical purity can be prepared through conventional after-treatment in a high yield manner.

Description

technical field [0001] The invention belongs to the technical fields of biological pharmacy and biochemical industry, and in particular relates to a method for preparing enantiomerically pure (S)-4-decanol through enzymatic asymmetric reduction. Background technique [0002] (S)-4-Decanol (as shown in Formula II) is a common and widely used chiral alcohol. Since the chiral center of chiral alcohol is connected with an active hydroxyl functional group, this kind of substance becomes a key chiral intermediate in the synthesis of many important chiral drugs, agricultural chemicals and natural products. For example, (S)-4-decanol is an important chiral intermediate for the preparation of a drug that inhibits astrocyte activation, and its chemical and optical purity determine the final quality of the chiral drug, so the improvement of its preparation method very important. [0003] [0004] At present, among the methods for preparing (S)-4-decanol (including traditional chem...

Claims

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Application Information

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IPC IPC(8): C12P7/04
CPCC12P7/04
Inventor 孙丰来李杰蔡小飞林金光陶海军戴匡初朱景仰
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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