Biocatalytic C7 Monomer Production Pathway

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Solution Overview

Problem

There is a lack of economically cost-competitive petrochemical routes for producing monomers for Nylon 7 and Nylon 7,7, necessitating a sustainable biocatalytic approach to synthesize 7-aminoheptanoate, pimelic acid, 7-hydroxyheptanoate, heptamethylenediamine, and 1,7-heptanediol.

Innovation Solution

The use of polypeptides with specific enzymatic activities such as β-ketoacyl synthase, β-ketothiolase, 3-hydroxyacyl-CoA dehydrogenase, and other enzymes to biosynthesize these compounds through biochemical pathways in microorganisms, enabling the conversion of N-acetyl-5-amino-3-oxopentanoyl-CoA to 7-aminoheptanoate and subsequent conversion to other C7 building blocks like pimelic acid, 7-hydroxyheptanoate, and heptamethylenediamine.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If biocatalytic methods are used to produce C7 building blocks, then sustainability and economic competitiveness are improved, but process complexity increases due to multiple enzymatic steps required

Engineering Contradiction:
Improveeconomic competitivenessVSAvoidprocess complexity
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The biocatalytic pathway is divided into distinct enzymatic segments, each catalyzing a specific transformation step from N-acetyl-5-amino-3-oxopentanoyl-CoA through various intermediates to final C7 building blocks. This segmentation allows for modular optimization of each enzymatic step while maintaining overall pathway functionality and economic viability

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent employs a multi-functional enzymatic system where different polypeptides with specific activities (β-ketoacyl synthase, β-ketothiolase, dehydrogenase, hydratase, reductase, thioesterase, CoA-transferase, deacetylase, transaminase) work together in an integrated pathway. Each enzyme performs a specialized function that contributes to the overall production of multiple C7 building blocks from a common precursor, achieving universality in substrate utilization

Inventive Principle:
Principle #6Universality (Multi-functionality)

2Adaptability or versatility

If multiple enzymatic conversion steps are implemented, then product diversity (multiple C7 building blocks) is improved, but manufacturing time and process duration increase

Engineering Contradiction:
Improveproduct diversityVSAvoidmanufacturing time
Core Design Contradiction:
Adaptability or versatilityVSLoss of time

Solution Approach 1:

The pathway is designed to produce N-acetyl-5-amino-3-oxopentanoyl-CoA as a centralized intermediate that can be diverted to multiple product streams. This preliminary formation of a versatile intermediate allows subsequent branching to different C7 building blocks (7-aminoheptanoate, pimelic acid, 7-hydroxyheptanoate, heptamethylenediamine, 1,7-heptanediol) without requiring separate complete pathways for each product, thereby reducing overall manufacturing time

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The biocatalytic pathway exhibits dynamic flexibility where enzyme expression levels, substrate availability, and product formation rates can be adjusted to optimize for different target products. The system can dynamically route metabolic flux toward different C7 building blocks based on demand, allowing versatile product production while minimizing total process duration through optimized pathway control

Inventive Principle:
Principle #15Dynamics

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 provides a sustainable and efficient biocatalytic route for producing C7 building blocks, overcoming the economic limitations of petrochemical methods and enabling the production of essential monomers for Nylon synthesis.

Implementation Method 1

enzymatically converting N-acetyl-5-amino-3-oxopentanoyl-CoA or a salt thereof to 7-aminoheptanoic acid or a salt thereof using one or more polypeptides having the activity of a 3-hydroxyacyl-CoA dehydrogenase, an enoyl-CoA hydratase, a trans-2-enoyl-CoA reductase, a β-ketothiolase, a thioesterase or a CoA-transferase and a deacetylase or methods using microorganisms expressing one or more of such enzymes

Methodology Applied
Scientific EffectEnzyme catalysis: Enzyme

Data Source

PatentUS11505814B2Methods and materials for producing 7-carbon monomers
Publication Date: 2022.11.22 INV NYLON CHEMICALS AMERICAS LLC
  • US11505814B2 patent drawing
  • US11505814B2 patent drawing
  • US11505814B2 patent drawing

AI summary

This document describes biochemical pathways for producing 7-aminoheptanoic acid using a β-ketoacyl synthase or a β-ketothiolase to form an N-acetyl-5-amino-3-oxopentanoyl-CoA intermediate. 7-aminoheptanoic acid can be enzymatically converted to pimelic acid, 7-hydroxyheptanoic acid, heptamethylenediamine or 1,7-heptanediol or corresponding salts thereof. This document also describes recombinant microorganisms producing 7-aminoheptanoic acid as well as pimelic acid, 7-hydroxyheptanoic acid, heptamethylenediamine and 1,7-heptanediol or corresponding salts thereof.