Journal
JOURNAL OF CHROMATOGRAPHY A
Volume 1246, Issue -, Pages 137-144Publisher
ELSEVIER SCIENCE BV
DOI: 10.1016/j.chroma.2012.05.002
Keywords
Cyclohexylcarbamate; Polysaccharide; Immobilization; Chiral packing material (CPM); Chiral stationary phase; High-performance liquid chromatography (HPLC); Thin-layer chromatography (TLC)
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The cyclohexylcarbamates of cellulose and amylose bearing a controlled amount of 3-(triethoxysilyl)propyl residue were synthesized by a one-pot process and efficiently immobilized onto silica gel through the intermolecular polycondensation of triethoxysilyl group. Their chiral recognition abilities were evaluated as chiral packing materials (CPMs) for high-performance liquid chromatography (HPLC). The immobilized CPMs exhibited comparable or higher recognition abilities than the conventional coated-type CPMs. The universal solvent compatibility of the immobilized CPMs clearly contributes to the improvement of chiral recognition for most racemates used in the present study. Interestingly, a significantly improved resolution for racemic trans-stilbene oxide (alpha = 2.23) could be attained on the immobilized CPM using the eluent containing 30 vol.% chloroform in hexane, which cannot be used for the conventional coated-type CPMs. On the CPMs, almost no resolution of trans-stilbene oxide was attained by a typical eluent, hexane-2-propanol mixture (90/10, v/v). The novel immobilized CPM can also be used in thin-layer chromatography (TLC) due to the absence of an aromatic group. (C) 2012 Elsevier B.V. All rights reserved.
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