Boranophosphate Oligomer Synthesis via Stereoselective Polymerizable Compound
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Solution Overview
Problem
Current methods for synthesizing boranophosphate oligomers face challenges in stereoselective synthesis, particularly in controlling the stereoisomers of the phosphorus atom and synthesizing oligomers with bases having amino groups, leading to low reactivity and difficulty in producing long chain oligomers.
Innovation Solution
A polymerizable compound with a novel structure, represented by specific formulas, is used to enable highly reactive and stereoselective synthesis of boranophosphate oligomers, allowing for the combination of different base species regardless of whether they have an amino group, and facilitating the production of long chain oligomers through a condensation method.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If conventional methods are used to synthesize boranophosphate oligomers, then synthesis can be performed, but stereoselectivity is poor and reactivity is low
Solution Approach 1:
The patent changes the chemical structure parameters of the phosphorus atom by introducing specific substituents (R1-R6 groups) and modifying the phosphodiester backbone to create a novel boranophosphate structure. This structural parameter change enables both high stereoselectivity in synthesis and high reactivity, resolving the contradiction between manufacturing precision and productivity
2Manufacturing precision
If steric control of phosphorus atom is implemented, then stereoselectivity improves, but side reactions occur in base moiety protected by protecting groups
Solution Approach 1:
The patent uses specific protecting groups as intermediaries that can be selectively removed under mild conditions. The protecting groups on base moieties are designed to be compatible with the stereoselective synthesis conditions, allowing stereocenter formation without triggering side reactions, thus resolving the contradiction between manufacturing precision and harmful factors
3Object-generated harmful factors
If protecting groups are removed under acidic conditions, then base moiety side reactions are avoided, but synthesis of long chain oligomers becomes difficult
Solution Approach 1:
The patent employs stepwise condensation methodology where the oligomer is built segment by segment through controlled coupling reactions. This segmentation allows the use of mild acidic conditions for protecting group removal at each step without compromising the overall chain elongation, resolving the contradiction between eliminating side reactions and achieving long chain synthesis
4Reliability
If conventional phosphodiester structures are used, then nucleic acid oligomer properties are maintained, but nuclease resistance and RNA affinity are insufficient
Solution Approach 1:
The patent creates a composite structure by replacing the conventional phosphodiester linkage with a boranophosphate linkage, combining elements of phosphorus chemistry with boron coordination. This composite chemical structure provides enhanced nuclease resistance while maintaining chemical stability, resolving the contradiction between reliability and compositional stability
Data Source
AI summary
Provided is a polymerizable compound represented by a Formula E-1 or Formula E-2 shown in the description. In Formula E-1 or Formula E-2, R1 represents an alkoxy group, —NRN2, a hydroxy group, an aryl group, or an alkyl group, wherein RN each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; n represents an integer from 1 to 5; R3 represents a hydrogen atom, an acetyl group, a phenoxyacetyl group, a pivaloyl group, a benzyl group, a 4-methoxybenzyl group, a benzoyl group, a triphenylmethyl group, a 4,4′-dimethoxytrityl (DMTr) group, a 4-methoxytrityl (MMTr) group, a 9-phenylxanthenyl group, a trimethylsilyl group, a cyanomethoxymethyl group, a 2-(cyanoethoxy)ethyl group, or a cyanoethoxymethyl group; and X represents a structure represented by any one of Formula B-1 to Formula B-5 shown in the description.