title: Enantiomeric separation of (R, S)-naproxen by recycling high speed counter-current chromatography with hydroxypropyl-β-cyclodextrin as chiral selector.
abstract: Recycling high speed counter-current chromatography (HSCCC) was successfully applied to resolution of (R, S)-naproxen (NAP) using hydroxypropyl-β-cyclodextrin (HP-β-CD) as chiral selector. The two-phase solvent system composed of n-hexane-ethyl acetate-0.1 mol L(-1) phosphate buffer solution with pH=2.67 (8:2:10, v/v/v) was selected. Influence factors for the chiral separation process were investigated, including concentration of HP-β-CD, equilibrium temperature and pH of aqueous phase. Suitable elution mode was selected for HSCCC enantioseparation of (R, S)-NAP. Under optimum separation conditions, 29 mg of (R, S)-NAP was separated using preparative recycling HSCCC with the molar ratio HP-β-CD/NAP racemate 83:1. Technical details for recycling elution mode were discussed as for chiral HSCCC separation. The purities of both (S)-NAP and (R)-NAP were over 99.5% as determined by HPLC. Enantiomeric excess of (S)-NAP and (R)-NAP reached 99.4%. Recovery for NAP enantiomers from HSCCC fractions was 82-89%, yielding 13 mg of (S)-NAP and 12 mg of (R)-NAP.
authors: Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China.
authors: Shengqiang
authors: S
authors: Tong
authors: Yi-Xin
authors: YX
authors: Guan
authors: Jizhong
authors: J
authors: Yan
authors: Bei
authors: B
authors: Zheng
authors: Liying
authors: L
authors: Zhao
mesh_terms: D000073738:2-Hydroxypropyl-beta-cyclodextrin; D000042:Absorption; D003377:Countercurrent Distribution / Q000295:instrumentation / Q000379:methods*; D009288:Naproxen / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D047392:beta-Cyclodextrins; D000073738:2-Hydroxypropyl-beta-cyclodextrin; D009288:Naproxen