Chiral enantiopure organosilane precursors for the synthesis of periodic mesoporous organosilicas

Cohen, Orit; Abu‐Reziq, Raed; Gelman, Dmitri

doi:10.1016/j.tetasy.2017.10.032

Cited by 5 publications

(2 citation statements)

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“…Few examples in the literature illustrate the potential of amino-amides (Si-AA) moieties to prevent protein adsorption on nanoparticles by zwitterionic coating based on silylated cysteine [20] or also to increase specificity toward a target through the formation of imprinted polymers [21]. In most cases, the silyl moiety was introduced by the reaction between 3isocyanatopropyltriethoxysilane and amine to yield urea function [17,18,22].…”

Section: Introductionmentioning

confidence: 99%

“…Innovative CE materials development should not only allow to tune the EOF and to limit or generate nonspecific adsorption but also to redesign the separations based on selective interactions (specific adsorption) for the analysis of proteins. Among the different ligands than can be incorporated in innovative materials (electrical conductivity [17], chirality [18], and sensitivity of pH response [19]), silylated amino‐acids (AA), and derivatives have been used to modulate properties of protein–protein interactions of silica materials, using mainly 3‐isocyanatopropyltriethoxysilane to introduce silyl moiety. AA recapitulates all types of weak interactions (π–π stacking, ionic, Van der Waals, etc.…”

Section: Introductionmentioning

confidence: 99%

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A bioinspired approach for the modulation of electroosmotic flow and protein–surface interactions in capillary electrophoresis using silylated amino‐amides blocks and covalent grafting

Gouyon,

Clavié,

Raquel

et al. 2023

Electrophoresis

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We explore a bioinspired approach to design tailored functionalized capillary electrophoresis (CE) surfaces based on covalent grafting for biomolecules analysis. First, the approach aims to overcome well‐known common obstacles in CE protein analysis affecting considerably the CE performance (asymmetry, resolution, and repeatability) such as the unspecific adsorption on fused silica surface and the lack of control of electroosmotic flow (EOF). Then, our approach, which relies on new amino‐amide mimic hybrid precursors synthesized by silylation of amino‐amides (Si–AA) derivatives with 3‐isocyanatopropyltriethoxysilane, aims to recapitulate the diversity of protein–protein interactions (π–π stacking, ionic, Van der Waals…) found in physiological condition (bioinspired approach) to improve the performance of CE protein analysis (electrochromatography). As a proof of concept, these silylated Si–AA (tyrosinamide silylation, serinamide silylation, argininamide silylation, leucinamide silylation, and isoglutamine silylation acid) have been covalently grafted in physiological conditions in different amount on bare fused silica capillary giving rise to a biomimetic coating and allowing both the modulation of EOF and protein–surface interactions. The analytical performances of amino‐amide functionalized capillaries were assessed using lysozyme, cytochrome C and ribonuclease A and compared to traditional capillary coatings poly(ethylene oxide), poly(diallyldimethylammonium chloride), and sodium poly(styrenesulfonate). EOF, protein adsorption rate, protein retention factor k, and selectivity were determined for each coating. All results obtained showed this approach allowed to modulate the EOF, reduce unspecific adsorption, and generate specific interactions with proteins by varying the nature and the amount of Si–AA in the functionalization mixture.

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