Enantiomeric separation of (R, S)-naproxen by recycling high speed counter-current chromatography with hydroxypropyl-β-cyclodextrin as chiral selector
Enantiomeric separation of (R, S)-naproxen by recycling high speed counter-current chromatography with hydroxypropyl-β-cyclodextrin as chiral selector
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DOI：
10.1016/j.chroma.2011.06.015
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发表时间：
2011-08-12
影响因子：
4.1
通讯作者：
Zhao, Liying
中科院分区：
文献类型：
--
作者：
Tong, Shengqiang;Guan, Yi-Xin;Zhao, Liying
以羟丙基-β-环糊精（HP-β-CD）为手性选择剂，采用循环高速逆流色谱法（HSCCC）拆分了（R，S）-萘普生（NAP）。选择了正己烷-乙酸乙酯-0.1 mol L-1磷酸盐缓冲液（pH = 2.67）（8：2：10，v/v/v）组成的两相溶剂体系。考察了HP-β-CD浓度、平衡温度和水相pH值等因素对手性分离过程的影响。选择了合适的洗脱方式，用于（R，S）-NAP的HSCCC对映体拆分。在最佳分离条件下，使用HP-β-CD/NAP外消旋物摩尔比为83：1的制备性再循环HSCCC分离29 mg（R，S）-NAP。讨论了手性HSCCC分离中循环洗脱模式的技术细节。经HPLC测定，（S）-NAP和（R）-NAP的纯度均在99.5%以上。（S）-NAP和（R）-NAP的对映体过量均达到99.4%。从HSCCC级分中回收NAP对映体为82- 89%，得到13 mg（S）-NAP和12 mg（R）-NAP。(C)2011 Elsevier B. V.保留所有权利。
Recycling high speed counter-current chromatography (HSCCC) was successfully applied to resolution of (R, S)-naproxen (NAP) using hydroxypropyl-beta-cyclodextrin (HP-beta-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-beta-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-beta-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. (C) 2011 Elsevier B.V. All rights reserved.