HPLC of fluoroquinolone antibacterials using chiral stationary phase based on enantiomeric (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6.
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.
Choi
Hee Jung
HJ
Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan, South Korea. Fax: +82-51-516-7421.
Cho
Hwan Sun
HS
Han
Sang Cheol
SC
Hyun
Myung Ho
MH
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
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