Macrocyclic Lactone Production Using Selective BVMO Oxidation
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Solution Overview
Problem
Existing methods for converting unsaturated macrocyclic ketones to lactones are inefficient and non-selective, often leading to the oxidation of the double bond, and are limited to small molecules due to the size of macrocyclic compounds.
Innovation Solution
The use of Baeyer-Villiger monooxygenase (BVMO) enzymes, either in cell-free enzyme formulations or whole cells, to catalyze the conversion of unsaturated macrocyclic ketones to lactones, ensuring high selectivity for the carbonyl group oxidation and providing reasonable yields.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If chemical oxidation methods are used to convert unsaturated macrocyclic ketones to lactones, then the conversion can proceed, but the selectivity is poor and double bond oxidation occurs as a frequent side reaction
Solution Approach 1:
The patent introduces an enzymatic intermediary (Baeyer-Villiger monooxygenase) to mediate the oxidation reaction. This enzyme selectively catalyzes the oxidation of the carbonyl group while leaving the double bond intact, thereby resolving the selectivity issue inherent in direct chemical oxidation methods.
Solution Approach 2:
The patent changes the reaction parameters by transitioning from chemical catalysts to biological enzymes. This parameter change fundamentally alters the reaction selectivity, enabling high-selectivity oxidation of the carbonyl group without affecting the double bond, thus eliminating the harmful side reactions.
2Manufacturing precision
If zeolite oxidation is used to improve selectivity for carbonyl group oxidation, then selectivity increases, but the method is limited to small molecules and cannot process macrocyclic compounds
Solution Approach 1:
The patent replaces the zeolite intermediary with an enzymatic intermediary (Baeyer-Villiger monooxygenase). This enzymatic mediator overcomes the size limitation of zeolites by providing a flexible active site that can accommodate macrocyclic substrates while maintaining high selectivity for carbonyl group oxidation.
Solution Approach 2:
The patent changes the catalyst type from inorganic zeolite to biological enzyme, which fundamentally alters the size and flexibility parameters. This enables the oxidation method to process macrocyclic compounds with large molecular sizes while preserving the high selectivity characteristic of zeolite oxidation.
3Productivity
If existing biotechnological methods are used for small unsaturated rings, then conversion to lactones is achieved, but side reactions including double bond oxidation still occur and the method is not applicable to macrocyclic systems
Solution Approach 1:
The patent employs a specifically engineered Baeyer-Villiger monooxygenase as the catalytic intermediary. This enzyme has been optimized to recognize and selectively oxidize the carbonyl group in macrocyclic substrates, preventing the non-selective side reactions that plague existing biotechnological methods.
Solution Approach 2:
The patent changes the enzymatic parameters by selecting and optimizing specific Baeyer-Villiger monooxygenases that exhibit high activity and selectivity for macrocyclic substrates. This parameter optimization enables both high productivity in lactone conversion and high selectivity by preventing double bond oxidation.
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
The method achieves high selectivity and yield in converting unsaturated macrocyclic ketones to lactones, avoiding double bond oxidation, applicable to various macrocyclic systems and enabling the production of novel fragrance molecules.
Implementation Method 1
the conversion is catalyzed by a Baeyer-Villiger monooxygenase
Implementation Method 2
oxidation of the carbonyl function
Data Source
AI summary
The present invention relates to methods for converting unsaturated macrocyclic ketones to lactones wherein the conversion is catalyzed by a Baeyer-Villiger monooxygenase (BVMO). The invention also relates to the use of a Baeyer-Villiger monooxygenase for the conversion of unsaturated macrocyclic ketones to lactones and provides certain novel macrocyclic lactones, which are accessible by the method according to the invention. Furthermore, the present invention relates to the use of novel and known macrocyclic lactones as fragrances.