Enzymatic Synthesis of 4-(Aminomethyl)Cyclohexane-1-Carboxylic Acid
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Solution Overview
Problem
Existing methods for producing 4-(aminomethyl)cyclohexane-1-carboxylic acid, such as chemical synthesis and microbial conversion, face challenges of high energy costs, environmental impact, and low productivity due to unidentified enzymes.
Innovation Solution
An enzymatic reaction pathway involving aminotransferase, aldehyde dehydrogenase, and choline oxidase is used to convert 1,4-bis(aminomethyl)cyclohexane or 1,4-cyclohexanedimethanol into 4-(aminomethyl)cyclohexane-1-carboxylic acid, utilizing specific proteins with desired activities expressed in E. coli strains.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If chemical synthesis methods are used to produce 4-(aminomethyl)cyclohexane-1-carboxylic acid, then the production can be carried out with established reaction pathways, but high temperature and high pressure are required resulting in high energy costs and large environmental load
Solution Approach 1:
The patent replaces the chemical synthesis method requiring high temperature and pressure with an enzymatic reaction system. The enzyme catalysts (aminotransferase and aldehyde dehydrogenase) enable the transformation to proceed under mild conditions, substituting the mechanical/thermal energy input with biological catalysis, thereby reducing energy consumption while maintaining reliable production
Solution Approach 2:
The patent changes the reaction conditions from high temperature and high pressure (chemical synthesis parameters) to mild temperature and neutral pH (enzymatic reaction parameters). This parameter change allows the same transformation to occur with significantly reduced energy input, resolving the contradiction between reliable production and energy efficiency
2Reliability
If chemical synthesis methods are used to produce 4-(aminomethyl)cyclohexane-1-carboxylic acid, then the production can be carried out with established reaction pathways, but high temperature and high pressure are required resulting in large environmental load
Solution Approach 1:
The patent replaces the chemical synthesis method requiring high temperature and pressure with an enzymatic reaction system. The enzyme catalysts (aminotransferase and aldehyde dehydrogenase) enable the transformation to proceed under mild conditions, substituting the mechanical/thermal energy input with biological catalysis, thereby reducing energy consumption while maintaining reliable production
Solution Approach 2:
The patent converts the harmful effects of high temperature and pressure (which cause energy waste and environmental pollution) into beneficial mild conditions by introducing enzyme catalysts. The enzymatic system achieves the same transformation with reduced harmful factors, turning the previous harmful reaction conditions into an environmentally friendly process
3Object-affected harmful factors
If microbial conversion method using Corynebacterium or Nocardia is used to produce trans-4-(aminomethyl)cyclohexane-1-carboxylic acid, then the production avoids high temperature and high pressure, but the productivity is low because the enzymes responsible have not been identified
Solution Approach 1:
The patent extracts the responsible enzymatic functions from the complex microbial system. By identifying and isolating the specific enzymes (aminotransferase and aldehyde dehydrogenase) that catalyze the transformation, the patent separates the catalytic activity from the whole microorganism, enabling the reaction to proceed with purified enzymes that can be optimized for high productivity
Solution Approach 2:
The patent segments the microbial conversion process into discrete enzymatic steps. Instead of relying on the entire microbial cell system, the reaction is divided into specific catalytic functions (aminotransferase step and aldehyde dehydrogenase step), each of which can be independently optimized and combined to achieve high productivity under mild conditions
4Object-affected harmful factors
If microbial conversion method using Corynebacterium or Nocardia is used to produce trans-4-(aminomethyl)cyclohexane-1-carboxylic acid, then the production avoids high temperature and high pressure, but the productivity is low because the enzymes responsible have not been identified
Solution Approach 1:
The patent introduces specific enzyme intermediaries (aminotransferase and aldehyde dehydrogenase) that mediate the transformation. These enzymes act as catalysts that facilitate the conversion from 1,4-bis(aminomethyl)cyclohexane to trans-4-(aminomethyl)cyclohexane-1-carboxylic acid under mild conditions, overcoming the low productivity issue by providing efficient catalytic pathways
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
This method allows for efficient production of 4-(aminomethyl)cyclohexane-1-carboxylic acid under mild conditions, reducing costs and environmental impact, while achieving high productivity and selective synthesis of desired stereoisomers.
Implementation Method 1
a protein having aminotransferase activity of converting an amino group of 1,4-bis(aminomethyl)cyclohexane into an aldehyde group to produce 4-(aminomethyl)cyclohexane-1-carbaldehyde
Implementation Method 2
a protein having aldehyde dehydrogenase activity of converting an aldehyde group of 4-(aminomethyl)cyclohexane-1-carbaldehyde into a carboxy group to produce 4-(aminomethyl)cyclohexane-1-carboxylic acid
Implementation Method 3
a protein having activity of converting a hydroxy group of a compound having the hydroxy group into an aldehyde group
Data Source
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AI summary
A production method of an embodiment is a method for producing cis- and/or trans-4-(aminomethyl)cyclohexane-1-carboxylic acid in the presence of at least one enzyme selected from the group consisting of a protein having activity of converting a hydroxy group into an aldehyde group, a protein having activity of converting an aldehyde group into a carboxy group, and a protein having activity of reversibly converting an aldehyde group and an amino group, using a compound represented by following general formula (1) as a substrate compound or an intermediate compound. [In the formula, R1 and R2 are each independently CH2OH, CHO, COOH, or CH2NH2 (provided that the case where one of R1 and R2 is COOH and the other is CH2NH2, and the case where both R1 and R2 are COOH, are excluded).] Specifically, the compound represented by the above general formula (1) is any one of Compounds 1, 2, 3, 4, 5, 6, 7, or 8.