One‐step strategy for the synthesis of a derivatized cyclodextrin‐based monolithic column

• Published in: Journal of separation science Vol. 37; no. 14; pp. 1720 - 1727
• Main Authors: Guo, Jialiang, Zhang, Qiaoxuan, Yao, Zhe, Zhao, Xianglong, Ran, Danni, Crommen, Jacques, Jiang, Zhengjin
• Format: Journal Article Web Resource
• Language: English
• Published: Weinheim Wiley-VCH 01.07.2014; Blackwell Publishing Ltd; Wiley; Wiley Subscription Services, Inc
• Subjects: Analysis; Analytical chemistry; beta-cyclodextrin; beta-Cyclodextrins - chemical synthesis; beta-Cyclodextrins - chemistry; beta-Cyclodextrins/chemical synthesis/chemistry; Biological and medical sciences; Cadmium; Chemical engineering; Chemical synthesis; Chemistry; Chromatographic methods and physical methods associated with chromatography; Chromatography; Chromatography, High Pressure Liquid - instrumentation; Click Chemistry; Columns (structural); Derivatized beta-cyclodextrin; Derivatized β-cyclodextrin; drugs; enantiomers; Exact sciences and technology; Fourier transform infrared spectroscopy; Fourier transforms; General pharmacology; high performance liquid chromatography; Human health sciences; hydrophilic interactions; Liquid chromatography; Mass spectrometry; Medical sciences; Methacrylates - chemistry; methylation; Monolithic columns; Monomers; non-polar compounds; Nucleosides; Other chromatographic methods; Peptides; Pharmacie, pharmacologie & toxicologie; Pharmacology. Drug treatments; Pharmacy, pharmacology & toxicology; physicochemical properties; scanning electron microscopy; Sciences de la santé humaine; Separation; Strategy; Capillary column; Performance evaluation; Purine derivatives; Fourier transformation; Separation; Chromatographic retention; HPLC chromatography; Mass copolymerization; Derivatization; Retention time; Characterization; Crosslinked copolymer; Functionalization; Enantiomer; Nucleoside; Derivatized β-cyclodextrin; Click chemistry; Stationary phase; Alkanophenone; Hydrophilic Interaction Liquid chromatography; Oligosaccharide; Monolithic column; Chiral stationary phase; Acebutolol; Ketone; Monolithic columns; Infrared spectrometry; Reversed phase chromatography; Cyclodextrin; Ultraviolet detector; Optical resolution; Preparation; Pyrimidine derivatives; Methacrylate copolymer; Inclusion compound; Radical copolymerization; Mass spectrometry; Apolar compound; Beta blocking agent
• ISSN: 1615-9306; 1615-9314; 1615-9314
• DOI: 10.1002/jssc.201400312

Derivatized β‐cyclodextrin (β‐CD) functionalized monolithic columns were prepared by a “one‐step” strategy using click chemistry. First, the intended derivatized β‐CD monomers were synthesized by a click reaction between propargyl methacrylate and mono‐6‐azido‐β‐CD and then sulfonation or methylation was carried out. Finally, monolithic columns were prepared through a one‐step in situ copolymerization of the derivatized β‐CD monomer and ethylene glycol dimethacrylate. The sulfated β‐CD‐based monolith was successfully applied to the hydrophilic interaction liquid chromatography separation of nucleosides and small peptides, while the methylated β‐CD‐functionalized monolith was useful for the separation of nonpolar compounds and drug enantiomers in capillary reversed‐phase liquid chromatography. The structures of the monomers were characterized by Fourier transform infrared spectroscopy and mass spectrometry. The physicochemical properties and column performance of monoliths were evaluated by scanning electron microscopy and micro high performance liquid chromatography. This strategy has considerable prospects for the preparation of other derivatized CD‐functionalized methacrylate monoliths.