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Method for reducing ketone compound by using two alcohol dehydrogenases

A technology of ketone compounds and alcohol dehydrogenase, which is applied in the field of reducing ketone compounds with two kinds of alcohol dehydrogenase, can solve the problems of limited application range, harsh reaction conditions, unnatural products, etc., and achieve safe and stable process conditions , mild reaction conditions and simple reaction steps

Active Publication Date: 2013-06-05
ASYMCHEM LAB TIANJIN +5
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Resolution is the most classic method for preparing chiral compounds, and the highest efficiency of classical and mainstream racemic compound resolution is no more than 50%. Although the process of chemical asymmetric synthesis is simple, the scope of application is limited, and chiral catalysts contain heavy metal pairs. Severe environmental pollution, harsh reaction conditions, high energy consumption, and non-natural products

Method used

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  • Method for reducing ketone compound by using two alcohol dehydrogenases
  • Method for reducing ketone compound by using two alcohol dehydrogenases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: the method for applying two kinds of alcohol dehydrogenases to reduce ketones is characterized in that the specific steps are as follows:

[0025] (1) Feeding: Add 5g (1eq) of the main raw material 3,4-dimethoxypropiophenone into a 250ml Erlenmeyer flask 50ml (10ml / g) phosphate buffer (50mmol / LpH=6.0), so that the substrate is evenly dispersed in the buffer;

[0026] (2) Alcohol dehydrogenase: continue to add 0.033g (0.0066g / g) reduced nicotinamide adenine dinucleotide, 0.05g (0.01g / g) alcohol dehydrogenase PAR and 25ml (5ml / g) of isopropanol, system pH=6.0;

[0027] (3) Reaction: The system was reacted in a shaker at 150rpm, and kept at 20±3°C for 24h;

[0028] (4) Post-treatment: filter the system with 50g (10g / g) of diatomaceous earth, extract with 100ml (20ml / g) of ethyl acetate, let stand to separate the liquid, dry the organic phase, filter, concentrate to obtain the crude product, and then pass through the column layer Analyze and purify to obta...

Embodiment 2

[0030] Embodiment 2: the method for applying two kinds of alcohol dehydrogenases to reduce ketones is characterized in that the specific steps are as follows:

[0031] (1) Feeding: Add 2g (1eq) of the main raw material N-tert-butoxycarbonyl-3-piperidone into a 250ml Erlenmeyer flask 40ml (20ml / g) phosphate buffer (50mmol / L, pH=7.0), to disperse the substrate evenly in the buffer;

[0032] (2) Alcohol dehydrogenase: continue to add 0.198g (0.099g / g) reduced nicotinamide adenine dinucleotide, 0.12g (0.06g / g) alcohol dehydrogenase PAR and 16ml (8ml / g) of isopropanol, system pH=7.0;

[0033] (3) Reaction: The system was reacted in a shaker at 200rpm, and kept at 20±3°C for 32h;

[0034] (4) Post-treatment: filter the system with 40g (20g / g) diatomaceous earth, extract with 60ml (30ml / g) dichloromethane, let stand to separate the liquid, dry the organic phase, filter, concentrate to get the crude product, and then pass through the column layer Analyze and purify to obtain the h...

Embodiment 3

[0035] Embodiment 3: the method for applying two kinds of alcohol dehydrogenases to reduce ketones is characterized in that the specific steps are as follows:

[0036] (1) Feeding: Add 2g (1eq) of the main raw material p-methylacetophenone into a 500ml Erlenmeyer flask 100ml (50ml / g) tris buffer (50mmol / L, pH=8.0), the substrate is evenly dispersed in the buffer;

[0037] (2) Alcohol dehydrogenase: Continue to add 0.248g (0.124g / g) reduced nicotinamide adenine dinucleotide phosphate, 0.2g (0.1g / g) alcohol dehydrogenase TeSADH and 40ml (20ml / g) of isopropanol, system pH=8.0;

[0038] (3) Reaction: The system was reacted in a shaker at 200rpm, and kept at 30±5°C for 45h;

[0039] (4) Post-treatment: filter the system with 50g (25g / g) diatomaceous earth, extract with 120ml (60ml / g) ethyl acetate, let stand to separate the liquid, dry the organic phase, filter, concentrate to get the crude product, and then pass through the column layer Analyze and purify to obtain 1.92g produc...

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Abstract

The invention discloses a method for reducing a ketone compound by using two alcohol dehydrogenases. Commercial materials in market or easy-to-obtain ketone compound are selected as initial raw materials, wherein R1 and R2 are respectively C1-C8 straight-chain alkyl, C5-C10 cycloalkyl, C5-C10 aryl or pyridyl group. The aryl or pyridyl group is not substituted or is substituted by one or more following groups: halogen, alkoxy or C1-C5 straight-chain alkyl. The reaction steps comprise feeding, dehydrogenase adding, reaction, and post-treatment. Especially, with the method, high-optical-purity chiral alcohol products can be obtained, and subsequent treatment purification operation is simple and safe. The method has the advantages of stable process condition, simple operation, and suitability for large-scale productions. Novel idea and method are provided for preparing chiral alcohol compounds.

Description

(1) Technical field: [0001] The invention relates to a method for reducing ketone compounds, in particular to a method for reducing ketone compounds by using two alcohol dehydrogenases. (2) Background technology: [0002] Biocatalysis refers to the process of chemical transformation using enzymes or biological organisms (whole cells, organelles, tissues, etc.) as catalysts, also known as biotransformation. It has very high stereoselectivity and is widely used in the synthesis of chiral compounds. Moreover, the variable cost of biocatalysis technology is low, easy to produce on a large scale, and the cost-effectiveness is relatively good. It has mild catalytic conditions, high catalytic efficiency, high substrate site, few by-products, and high yield, so it has become an important method for industrially synthesizing chemicals, pharmaceuticals and pesticide intermediates. Resolution is the most classic method for preparing chiral compounds, and the highest efficiency of clas...

Claims

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Application Information

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IPC IPC(8): C12P7/22C12P17/12C12P17/18
Inventor 洪浩郑长胜吕彤高峰李雁飞吕丽慧
Owner ASYMCHEM LAB TIANJIN
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