3'-Substituted Abscisic Acid Derivatives Synthesis
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Solution Overview
Problem
Current synthetic ABA derivatives face challenges in terms of low overall yields and high production costs due to multi-step de novo synthesis, limiting their commercial application, and there is a need for enantiomerically pure (S)-ABA derivatives and novel (±)-ABA derivatives with improved biological activities.
Innovation Solution
Development of new (S)-ABA and (±)-ABA derivatives with specific structural formulas (Formulas I and II) that can be synthesized efficiently, allowing for effective plant growth regulation and offering improved biological activities as agonists or antagonists.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If multi-step de novo synthesis is used to prepare ABA analogs, then structural diversity and biological activity can be achieved, but overall yield decreases and production cost increases
Solution Approach 1:
The patent uses (S)-ABA as a pre-synthesized starting material that already contains the core cyclohexenone ring structure. By performing substitution reactions on this pre-formed core, the patent avoids the need to construct the complex ring system during the synthesis, thereby reducing the number of steps and improving overall yield while maintaining structural diversity through various substituent options.
Solution Approach 2:
The patent divides the ABA molecule into a core structure ((S)-ABA) and substituent groups (R1, R2, R3). This segmentation allows the core to be synthesized once and reused, while only the substituent portions need to be varied to create different analogs. This approach reduces redundant synthesis steps and improves productivity.
2Adaptability or versatility
If multi-step de novo synthesis is used to prepare ABA analogs, then structural diversity can be achieved, but manufacturing cost increases
Solution Approach 1:
The patent uses (S)-ABA as a pre-synthesized starting material that already contains the core cyclohexenone ring structure. By performing substitution reactions on this pre-formed core, the patent avoids the need to construct the complex ring system during the synthesis, thereby reducing the number of steps and improving overall yield while maintaining structural diversity through various substituent options.
Solution Approach 2:
The patent achieves structural diversity by changing the substituent parameters (R1, R2, R3 groups) attached to the (S)-ABA core rather than redesigning the entire molecular structure each time. This allows for efficient exploration of different ABA analogs using standardized substitution reactions, reducing manufacturing complexity and cost.
3Reliability
If existing ABA derivatives are synthesized, then some biological activity can be achieved, but metabolic stability and tissue uptake are limited
Solution Approach 1:
The patent introduces specific substituent groups at defined positions (R1 at C3', R2 at C8', R3 at C10') of the ABA core structure. These localized modifications at specific positions allow for optimization of metabolic stability and tissue uptake properties while preserving the essential biological activity through maintenance of the core (S)-ABA structure and its key functional groups.
Data Source
AI summary
The invention relates to a novel class of (S)-3′-substituted-abscisic acid derivatives and (±)-3′-substituted-abscisic acid derivatives, and methods of synthesizing the derivatives.