Derivatized Cyclofructan Chiral Stationary Phases
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Solution Overview
Problem
Current chiral stationary phases (CSPs) for enantiomeric separations are limited in applicability, selectivity, and efficiency, with few types dominating the field, and cyclofructans have not been utilized effectively as CSPs due to their structural properties, such as high melting points and limited ability to form inclusion complexes.
Innovation Solution
Development of compositions and methods using derivatized cyclofructans covalently linked to solid supports, which serve as chiral stationary phases for chromatographic separations, enhancing separation capabilities through specific functionalization and linkage strategies.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If native cyclofructans are used as CSPs, then they can provide chiral separation capability, but their high melting points and limited ability to form inclusion complexes reduce their applicability and separation efficiency
Solution Approach 1:
The patent applies parameter changes by derivatizing cyclofructans with various chemical groups (e.g., permethylated, penta-O-acetyl, carbamate derivatives) to modify their physical and chemical properties. This derivatization reduces melting points, enhances solubility in different mobile phases, and improves inclusion complex formation capability, enabling use across normal phase, polar organic, and reversed phase chromatographic modes
Solution Approach 2:
The patent creates composite materials by combining derivatized cyclofructans with silica gel supports through covalent bonding. This composite approach integrates the chiral recognition capability of cyclofructans with the mechanical stability and surface area of silica gel, producing stationary phases that exhibit both superior enantiomeric separation and operational reliability
2Device complexity
If only a few types of CSPs are used, then device complexity is reduced, but broader applicability and superior separation properties for specific enantiomers are limited
Solution Approach 1:
The patent achieves universality by developing a platform of cyclofructan-based CSPs that can function across multiple chromatographic modes (normal phase, polar organic, reversed phase) and separate diverse enantiomer classes. The derivatized cyclofructans provide a common structural foundation that adapts to different separation requirements, reducing the need for completely different CSP types while expanding applicability
3Manufacturing precision
If derivatized cyclofructans are covalently linked to solid supports, then separation selectivity and efficiency are improved, but manufacturing complexity increases
Solution Approach 1:
The patent applies preliminary action by first derivatizing cyclofructans with desired functional groups before coupling them to silica gel supports. This sequential approach allows optimization of each step independently: derivatization conditions can be optimized for desired chiral recognition properties, then coupling conditions can be optimized for stable attachment to the support, simplifying the overall manufacturing process while maintaining high separation selectivity
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 use of derivatized cyclofructans as CSPs improves the separation of enantiomers by offering broader applicability, superior selectivity, and efficiency in various chromatographic modes, including normal phase, polar organic, and reversed phase modes, while maintaining stability across multiple injections.
Implementation Method 1
The present invention relates to compounds of formula I, compositions comprising compounds of formula I, and methods of using compositions comprising compounds of formula I for chromatographic separations of chemical species
Implementation Method 2
hydrophobic inclusion complexation, which plays an important role in the association of organic molecules with cyclodextrins
Data Source
AI summary
The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.