Cyclohexane Oligosaccharide Mimics for E-Selectin Antagonism
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Solution Overview
Problem
The production of monosaccharides and oligosaccharides is costly and complex, especially when mass production is required, and their mimics, or glycomimetics, do not significantly reduce production costs despite potentially improving biological properties.
Innovation Solution
Development of specific cyclohexane derivatives and their oligosaccharide mimics, which serve as antagonists of E-selectin, offering a cost-effective alternative through optimized synthesis pathways.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If monosaccharides and oligosaccharides are produced through conventional synthesis methods, then the desired biological compounds are obtained, but the production cost and complexity increase significantly
Solution Approach 1:
The patent creates simplified copies (glycomimetics) that replicate the essential biological function of complex monosaccharides and oligosaccharides. Instead of synthesizing the complete natural structures, the invention uses cyclohexane derivatives that copy only the critical features needed for E-selectin binding, dramatically reducing synthesis complexity while maintaining biological activity
Solution Approach 2:
The patent employs inexpensive cyclohexane-based building blocks and commercially available reagents to construct glycomimetics. The simplified molecular structure allows for cost-effective synthesis using standard chemical techniques, making the compounds economically viable compared to expensive natural product isolation or complex total synthesis
2Reliability
If glycomimetics are developed to improve biological properties, then biological activity may be enhanced, but production cost does not significantly reduce
Solution Approach 1:
The patent systematically varies structural parameters of the cyclohexane core and substituent groups to optimize both biological activity and synthesizability. By changing parameters such as hydroxyl group positioning, acetal bridge configuration, and side chain composition, the invention achieves high E-selectin affinity while maintaining simple, scalable synthesis routes
3Reliability
If complex oligosaccharide structures are synthesized, then biological function is achieved, but production time and process complexity increase
Solution Approach 1:
The patent divides the oligosaccharide mimic into discrete modular components (cyclohexane core, acetal bridge, hydroxyl groups, and substituent chains) that can be synthesized and assembled independently. This segmentation allows for parallel synthesis of building blocks and simplifies the overall production process, reducing total manufacturing time while maintaining biological function
Data Source
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AI summary
Compounds and methods are provided for obtaining oligosaccharide mimics. More specifically, compounds and methods are described wherein oligosaccharide mimics are obtained by incorporating or substituting in a cyclohexane derivative.