Highly efficient preparation of β-CD-based chiral monolithic column by "one-pot" hydroxymethyl polycondensation for enantioseparation in capillary liquid chromatography

Rongguo Chen; Chenchen Lin; Haixia Lyu; Xucong Lin; Zenghong Xie

doi:10.1016/j.chroma.2019.460781

Highly efficient preparation of β-CD-based chiral monolithic column by "one-pot" hydroxymethyl polycondensation for enantioseparation in capillary liquid chromatography

J Chromatogr A. 2020 Apr 12:1616:460781. doi: 10.1016/j.chroma.2019.460781. Epub 2019 Dec 10.

Authors

Rongguo Chen¹, Chenchen Lin², Haixia Lyu³, Xucong Lin⁴, Zenghong Xie⁵

Affiliations

¹ Institute of Food Safety and Environment Monitoring, Fuzhou University, Fuzhou, 350108, China; Institute of Chemical Safety, Fujian University of Technology, Fuzhou 350118, China.
² Institute of Food Safety and Environment Monitoring, Fuzhou University, Fuzhou, 350108, China.
³ College of Materials Science and Engineering, Fuzhou University, Fuzhou, 350108, China.
⁴ Institute of Food Safety and Environment Monitoring, Fuzhou University, Fuzhou, 350108, China. Electronic address: xulin@fzu.edu.cn.
⁵ Institute of Food Safety and Environment Monitoring, Fuzhou University, Fuzhou, 350108, China. Electronic address: zhxie@fzu.edu.cn.

PMID: 31858997
DOI: 10.1016/j.chroma.2019.460781

Abstract

A facile strategy for highly efficient fabrication of chiral monolithic column was carried out by the simple "one-pot" hydroxymethyl polycondensation of native β-cyclodextrin (β-CD) and urea-formaldehyde (UF). In-situ rapid substitution of native β-CD and efficient polycondensation of β-CD products and UF oligomers was proposed and fulfilled in one pot. The feasibility, mechanism and key parameters of polycondensation reaction were discussed. The data on crosslinking polycondensation and reaction kinetics were further evaluated. Characteristics including the morphologies, permeability and structure stability of the resultant monolithic columns were also studied. Under the optimal conditions, the "one-pot" hydroxymethyl polycondensation was accomplished in an aqueous solution within only 10 mins. Satisfactory stability and repeatability were gained, and good enantioseparation of eight model enantiomers was successfully achieved with the resultant β-CD-based monolith. It was simple and highly efficient, and the organic solvents, special CD derivatives and tediously long-time polymerization reaction were successfully avoided, which might light a new access to rapid preparation of CD-chiral monolith for high-performance enantioseparation.

Keywords: Chiral monolithic column; Enantioseparation; Hydroxymethyl polycondensation; Rapid preparation; β-cyclodextrin.

MeSH terms

Chemistry Techniques, Analytical / instrumentation*
Chemistry Techniques, Analytical / methods*
Chromatography, Liquid / instrumentation*
Permeability
Polymerization
Stereoisomerism
beta-Cyclodextrins / chemistry*

Substances

beta-Cyclodextrins
betadex