The interactions between chiral analytes and chitosan-based chiral stationary phases during enantioseparation

Chen, Wei; Jiang, Jizhou; Qiu, Guo‐Song; Tang, Sheng; Bai, Zheng‐Wu

doi:10.1016/j.chroma.2021.462259

Cited by 15 publications

(7 citation statements)

References 38 publications

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“…Although chromatography has become a fully fledged commercial technology of separation after decades of development, the development of CSPs presents significant room for improving chiral separation. In addition to the modified typical CSPs of cyclodextrin (CD), macrocyclic antibiotics, and polysaccharide, − many novel functional crystalline porous material based CSPs, including covalent–organic frameworks (COFs), metal–organic frameworks (MOFs), and porous organic cages (POCs) have started to show their up-and-coming brilliance for chromatographic separation of enantiomers. − …”

Section: Chromatographymentioning

confidence: 99%

Recent Advances in Separation and Analysis of Chiral Compounds

Yan

2023

Anal. Chem.

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Section: Chromatographymentioning

confidence: 99%

Recent Advances in Separation and Analysis of Chiral Compounds

Yan

2023

Anal. Chem.

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“…Recently, the impact of chlorine substitution was also explored for chitosan-based selectors by Bai and coauthors. 1390 In the context of a study on the enantioseparation of chiral analytes on six chitosan 3,6-bis(phenylcarbamate)-2-(cyclohexylmethylurea)s, the authors evaluated the acidity of the amide hydrogen of the phenylcarbamate derivatives at the DFT level, calculating and comparing the NBO charges of the amidic hydrogens of the chitosan-based CSPs.…”

Section: Computation-based Modelling Of Enantioseparation Processes A...mentioning

confidence: 99%

“…Modelling studies were also performed by using other polysaccharides as CSs. 1390,1409 El Deeb and co-authors reported a molecular docking analysis of the HPLC enantioseparations of amlodipine and verapamil by using a monolithic epoxy silica column containing chondroitin sulfate A as a CS. 1409 An environment determined by the helical secondary structure of a macromolecular selector decorated with side chains able to exert HB and π−π interactions also features peptoid-based selectors.…”

Section: Computation-based Modelling Of Enantioseparation Processes A...mentioning

confidence: 99%

“…Experimental ,,− and theoretical , studies demonstrated the impact of chlorine substitution of the aromatic pendant groups on the discrimination features of the selector and on its capability as HB donor (NH) and acceptor (CO). Recently, the impact of chlorine substitution was also explored for chitosan-based selectors by Bai and co-authors . In the context of a study on the enantioseparation of chiral analytes on six chitosan 3,6-bis(phenylcarbamate)-2-(cyclohexylmethylurea)s, the authors evaluated the acidity of the amide hydrogen of the phenylcarbamate derivatives at the DFT level, calculating and comparing the NBO charges of the amidic hydrogens of the chitosan-based CSPs.…”

Section: Trends In Enantioselective Recognition In Separation Science...mentioning

confidence: 99%

“…Modelling studies were also performed by using other polysaccharides as CSs. , El Deeb and co-authors reported a molecular docking analysis of the HPLC enantioseparations of amlodipine and verapamil by using a monolithic epoxy silica column containing chondroitin sulfate A as a CS …”

Section: Trends In Enantioselective Recognition In Separation Science...mentioning

confidence: 99%

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Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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It is not a coincidence that both chirality and noncovalent interactions are ubiquitous in nature and synthetic molecular systems. Noncovalent interactivity between chiral molecules underlies enantioselective recognition as a fundamental phenomenon regulating life and human activities. Thus, noncovalent interactions represent the narrative thread of a fascinating story which goes across several disciplines of medical, chemical, physical, biological, and other natural sciences. This review has been conceived with the awareness that a modern attitude toward molecular chirality and its consequences needs to be founded on multidisciplinary approaches to disclose the molecular basis of essential enantioselective phenomena in the domain of chemical, physical, and life sciences. With the primary aim of discussing this topic in an integrated way, a comprehensive pool of rational and systematic multidisciplinary information is provided, which concerns the fundamentals of chirality, a description of noncovalent interactions, and their implications in enantioselective processes occurring in different contexts. A specific focus is devoted to enantioselection in chromatography and electromigration techniques because of their unique feature as “multistep” processes. A second motivation for writing this review is to make a clear statement about the state of the art, the tools we have at our disposal, and what is still missing to fully understand the mechanisms underlying enantioselective recognition.

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Hybrid Supports for Oligonucleotide Synthesis: Controlled Pore Glass Derivatives with Branched Amine‐Ended Polyether or Polyimine

Trzciński,

Brzezinska,

Waligórski

et al. 2024

Chemistry A European J

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Controlled pore glass (CPG), differing in pore size and subsequent specific surface, was chemically modified by: (1) increasing surface susceptibility for amine functionalization via reaction with oxirane‐type (active) and alkyl/aryl‐type (inactive towards amine compounds) silane pro‐adhesive compounds, and (2) immobilization of trimethylolpropane tris[poly(propylene glycol), amine terminated] ether, comb‐like 8‐arm octa[poly(ethylene glycol) amine] with each branch amine terminated, and a poly(propylene imine) amine‐terminated second‐generation dendrimer. The increase in surface density of amine functions—monitored by UV‐Vis technique adopted for quantitative measurements of Ruhemann’s purple intensity—improved final loading capacity, characterized by dimethoxytrityl cation absorption. Obtained materials proved their applicability in automatic oligonucleotide (ON) synthesis, especially when silanized 2000 Å CPG modified with 8‐arm octa[poly(ethylene glycol) amine], with deduced empirical formula CPG—silane—(NH)5.7PEG‐(NH2)2.3, was used for long‐chain (150 nucleotides) ONs synthesis. This can be regarded as a good CPG support for this purpose. Moreover, hybrid supports with different porosity allowed the synthesis of shorter ONs with satisfactory yield and purity, monitored by RP‐HPLC and MALDI‐TOF. On the molecular level, two competitive mechanisms seem to influence the utility of the final hybrid support: spatial availability of active sites and the propensity of the functionalizer to bond with the CPG surface.

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The interactions between chiral analytes and chitosan-based chiral stationary phases during enantioseparation

Cited by 15 publications

References 38 publications

Recent Advances in Separation and Analysis of Chiral Compounds

Recent Advances in Separation and Analysis of Chiral Compounds

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Hybrid Supports for Oligonucleotide Synthesis: Controlled Pore Glass Derivatives with Branched Amine‐Ended Polyether or Polyimine

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