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Application of porcine pancreas alpha-amylase as catalyst of asymmetrical Mannich reaction

An amylase, asymmetric technology, applied in the field of chemistry, to achieve the effect of good catalytic activity, high yield and high ee value

Inactive Publication Date: 2012-07-04
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, the three-component asymmetric Mannich reaction of aromatic aldehydes, aromatic amines and ketones catalyzed by enzymes has not been reported at home and abroad.

Method used

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  • Application of porcine pancreas alpha-amylase as catalyst of asymmetrical Mannich reaction
  • Application of porcine pancreas alpha-amylase as catalyst of asymmetrical Mannich reaction
  • Application of porcine pancreas alpha-amylase as catalyst of asymmetrical Mannich reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1. Confirmation of the activity of porcine pancreatic α-amylase in catalyzing the three-component asymmetric Mannich reaction of aromatic aldehydes, aromatic amines and ketones

[0024] In this example, the reaction of p-nitrobenzaldehyde, aniline and cyclohexanone was used as a template reaction to confirm the activity of porcine pancreatic alpha-amylase in catalyzing the three-component asymmetric Mannich reaction of aromatic aldehydes, aromatic amines and ketones. The experimental method is as follows: add p-nitrobenzaldehyde (0.5 mmol), aniline (0.55 mmol) and cyclohexanone (5 mmol) into the reaction flask. * Is 15 mmol), no catalyst is added or catalyst (100 mg) is added, and water (0.15 ml) is added in Table 1. * It is 0.25 ml) and acetonitrile or 1,4-dioxane (1 ml). The temperature is controlled at 25°C and the reaction is stirred. After the reaction is completed, filter, wash the filter cake with ethyl acetate, combine the filtrate and washing liquid, dry w...

Embodiment 2

[0028] Example 2. Methodological study on the application of porcine pancreatic α-amylase to catalyze the three-component asymmetric Mannich reaction of aromatic aldehydes, aromatic amines and ketones

[0029] In this example, the reaction of p-nitrobenzaldehyde, aniline and cyclohexanone was used as a template reaction, and the main influencing factors (solvent, Water content, temperature, enzyme content and substrate feeding ratio) were systematically studied.

[0030] 1. The influence of solvent

[0031] Add p-nitrobenzaldehyde (0.5 mmol), aniline (0.55 mmol), cyclohexanone (5 mmol) and porcine pancreatic α-amylase (100 mg) to the reaction flask, and then add water (0.15 ml, the winning bid in Table 2) * It is 0.25 ml) and solvent (1 ml). The temperature is controlled at 25°C and the reaction is stirred for 120 hours. The post-treatment method is the same as in Example 1. The results are shown in Table 2.

[0032] Table 2 Effects of solvents on the asymmetric Mannich reaction cat...

Embodiment 3

[0055] Example 3. General investigation of the three-component asymmetric Mannich reaction of aromatic aldehyde, aromatic amine and ketone catalyzed by porcine pancreatic α-amylase

[0056] In this example, the versatility of the three-component asymmetric Mannich reaction of aromatic aldehydes, aromatic amines and ketones catalyzed by porcine pancreatic α-amylase was investigated. The experimental method is: add aromatic aldehyde (0.5 mmol), aromatic amine (0.55 mmol), cyclohexanone (15 mmol) or heterocyclic ketone (0.75 mmol) or acetone (30 mmol), porcine pancreatic α-starch into the reaction flask Enzyme (100 mg), then water (0.25 ml) and 1,4-dioxane (1 ml) were added, and the temperature was controlled at 25°C and the reaction was stirred. The post-treatment method was the same as in Example 1. The results are shown in Table 7.

[0057] Table 7 Porcine pancreatic α-amylase catalyzes the asymmetric Mannich reaction of aromatic aldehydes, aromatic amines and ketones

[0058]

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Abstract

The invention discloses application of porcine pancreas alpha-amylase as a catalyst of an asymmetrical Mannich reaction for three components, namely aromatic aldehyde, aromatic amine and ketone for the first time. The porcine pancreas alpha-amylase has the advantages of favorable catalytic activity, high enantioselectivity, environment friendliness, economy and the like. The invention further provides a method for applying the porcine pancreas alpha-amylase to catalyze the three components such as the aromatic aldehyde, the aromatic amine and the ketone to the asymmetrical Mannich reaction. The porcine pancreas alpha-amylase is high in yield and ee value and is broad in application prospect in the field of asymmetric synthesis; and according to the porcine pancreas alpha-amylase, the application range of the porcine pancreas alpha-amylase can be widened and a potential excellent catalyst for the asymmetrical Mannich reaction is provided.

Description

technical field [0001] The invention belongs to the field of chemistry, and relates to the new application of porcine pancreatic α-amylase in organic synthesis, in particular to the application of porcine pancreatic α-amylase as a three-component asymmetric Mannich reaction catalyst of aromatic aldehydes, aromatic amines and ketones, and the application Method for catalyzing the above-mentioned asymmetric Mannich reaction by porcine pancreatic alpha-amylase. Background technique [0002] With the deepening understanding of the molecular mechanism of drug interaction, chirality is becoming more and more important, which plays a crucial role in the effectiveness of drugs and agrochemicals. Therefore, it is of great significance to establish a suitable asymmetric synthesis method to obtain a single enantiomer product to promote the development of the pharmaceutical industry. [0003] Enzyme biocatalysts provide a highly selective tool for asymmetric synthesis. Due to the limi...

Claims

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Application Information

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IPC IPC(8): C12P13/00C12P17/00
Inventor 何延红官智徐可岭
Owner SOUTHWEST UNIVERSITY
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