HPLC of fluoroquinolone antibacterials using chiral stationary phase based on enantiomeric (3,3 '-diphenyl-1,1 '-binaphthyl)-20-crown-6
ABSTRACT A residual silanol group-protecting chiral stationary phase (CSP) based on optically active (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6 was successfully applied to the resolution of fluoroquinolone compounds including gemifloxacin mesylate. The chiral recognition ability of the residual silanol group-protecting CSP was generally greater than that of the residual silanol group-containing CSP. From these results, it was concluded that the simple protection of the residual silanol groups of the latter CSP with lipophilic n-octyl groups can improve its chiral recognition ability for the resolution of racemic fluoroquinolone compounds. The chromatographic resolution behaviors were investigated as a function of the content and type of organic and acidic modifiers and the ammonium acetate concentration in aqueous mobile phase and the column temperature. Especially, the addition of ammonium acetate to the mobile phase was found to be a quite effective means of reducing the enantiomer retentions without sacrificing the chiral recognition efficiency of the CSP.
SourceAvailable from: Myung Ho HyunBulletin- Korean Chemical Society 10/2012; 33(10). DOI:10.5012/bkcs.2012.33.10.3497 · 0.84 Impact Factor
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ABSTRACT: Two chiral stationary phases (CSPs) based on (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6 bonded covalently to silica gel were applied for the first time to the resolution of racemic vigabatrin and its analogue -amino acids and the resolution results were compared to those on the commercially available Crownpak CR(+) based on (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6 coated dynamically onto octadecylsilica gel. While vigabatrin was not resolved at all on Crownpak CR(+), it was resolved quite well on the two CSPs. Among four vigabatrin analogue -amino acids, only two were resolved on Crownpak CR(+), but three were resolved on the CSP (CSP 1) containing residual silanol groups and all of four were resolved on the CSP (CSP 2) containing residual silanol group-protecting n-octyl groups. The improved lipophilicity in CSP 2 was proposed to be responsible for its superiority to CSP 1 for the resolution of vigabatrin and analogue -amino acids. In addition, the composition of aqueous mobile phase was found to affect the chiral recognition behaviors for the resolution of vigabatrin and analogue -amino acids on CSP 2.Bulletin- Korean Chemical Society 08/2011; 32(spc8). DOI:10.5012/bkcs.2011.32.8.3017 · 0.84 Impact Factor
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ABSTRACT: Shanshan Yu was born in 1986 in Dezhou, Shandong Province, P. R. China. She received her B.S. degree in chemistry from Wuhan University in 2008. She then enrolled in the Department of Chemistry at University of Virginia in 2008. Under the supervision of Professor Lin Pu, she obtained her Ph.D. degree in 2013. In the same year, she was appointed as an associate professor in the College of Chemistry at Sichuan University. The research projects in her laboratory focus on the design and synthesis of novel chiral molecules and macromolecules for applications in enantioselective fluorescent sensors.Tetrahedron 02/2015; 71(5). DOI:10.1016/j.tet.2014.11.007 · 2.82 Impact Factor