Constructing chiral caves and efficiently separating enantiomers of glutamic acid with novel surface-imprinting technique

• Published in: Journal of Chromatography A Vol. 1218; no. 32; pp. 5441 - 5448
• Main Authors: Gao, Baojiao, Chen, Yingxin, Men, Jiying
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 12.08.2011; Elsevier
• Subjects: Analytical chemistry; binding capacity; Chemistry; Chromatographic methods and physical methods associated with chromatography; chromatography; Chromatography - instrumentation; Chromatography - methods; Crosslinking; Dimethylaminoethyl methacrylate; Enantiomer separation; Enantiomers; Exact sciences and technology; Glutamic acid; Glutamic Acid - chemistry; Glutamic Acid - isolation & purification; Graft polymerization; Grafting; Methacrylates - chemical synthesis; Methacrylates - chemistry; molecular conformation; Molecular Imprinting; Nylons - chemical synthesis; Nylons - chemistry; polymerization; Recognition; Selectivity; Separation; silica gel; Silicon dioxide; Silicon Dioxide - chemical synthesis; Silicon Dioxide - chemistry; Stereoisomerism; Surface-molecular imprinting; Dimethylaminoethyl methacrylate; Glutamic acid; Surface-molecular imprinting; Graft polymerization; Recognition; Enantiomer separation; Separation; Adsorption isotherm; Polymerization; Chiral recognition; Affinity adsorbent; Characterization; α-Aminoacid; Binding isotherm; Optical resolution; Enantiomer; Preparation; Crosslinked polymer; Electrokinetic potential; Silica gel; Molecular imprinting; Graft polymers
• ISSN: 0021-9673; 1873-3778
• DOI: 10.1016/j.chroma.2011.06.003

Dimethylaminoethyl methacrylate (DMAEMA) was first graft-polymerized onto the surfaces of micron-sized silica gel particles in the manner of “grafting from” in a solution polymerization system, obtaining the grafted particles PDMAEMA/SiO 2. Then, the molecular imprinting towards the grafted PDMAEMA was conducted with one enantiomer of glutamic acid (Glu), l-Glu, as template molecule and with 2,2′-dichlorodiethylether (DCEE) as crosslinking agent by adopting the novel surface-molecular imprinting technique established by our research group, and the single enantiomer ( l-Glu) molecule-imprinted material MIP-PDMAEMA/SiO 2 was obtained. With another enantiomer of glutamic acid, d-Glu, as the contrast compound, the recognition property of MIP-PDMAEMA/SiO 2 for l-Glu was investigated in depth with both static and dynamic methods, and its ability to separate l-Glu and d-Glu in the racemic solution was examined. The experiment results show that the surface-imprinted material MIP-PDMAEMA/SiO 2 has fine recognition selectivity and binding affinity for l-Glu, whereas its ability to combine d-Glu is poor. The selectivity coefficient of MIP-PDMAEMA/SiO 2 for l-Glu with respect to d-Glu is equal to 3.30, displaying an excellent chiral separation result. It is obvious that in this study, the substance separation at the molecular configuration level has been realized successfully.