title: 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.
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan, South Korea. Fax: +82-51-516-7421.
authors.forename: Hee Jung
authors.initials: HJ
authors.lastname: Choi
authors.forename: Hwan Sun
authors.initials: HS
authors.lastname: Cho
authors.forename: Sang Cheol
authors.initials: SC
authors.lastname: Han
authors.forename: Myung Ho
authors.initials: MH
authors.lastname: Hyun
mesh_terms: D000900:Anti-Bacterial Agents / Q000032:analysis* / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D043844:Crown Ethers / Q000737:chemistry*; D024841:Fluoroquinolones / Q000032:analysis* / Q000737:chemistry*; D000077735:Gemifloxacin; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D009287:Naphthyridines / Q000032:analysis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C530035:(3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6; D000900:Anti-Bacterial Agents; D043844:Crown Ethers; D024841:Fluoroquinolones; D009281:Naphthalenes; D009287:Naphthyridines; D000077735:Gemifloxacin