外消旋萘普生酯类在四种纤维素衍生物手性柱上的分离及手性识别机理研究  

Enantioseparation of Racemic Naproxen Esters on Four Cellulose Derivative Chiral Columns and Chiral Recognition Mechanism

作　　者：邵保海[1] 徐秀珠[1] 邹莉[1] 蔡小军[1] 傅小芸[1] 

机构地区：[1]浙江大学化学系,

出　　处：《化学学报》2001年第11期1982-1988,共7页Acta Chimica Sinica

摘　　要：在纯聚合物型的纤维素三醋酸酯(CTA)、纤维素三苯甲酸酯(CTB)与涂敷型的CTB、纤维素三(4-甲基苯甲酸酯)(CTMB)四种纤维素衍生物手性柱上成功地分离了几种外消旋萘普生酯,研究了流动相组成以及溶质的结构对手性分离的影响,探讨了纤维素衍生物手性固定相对外消旋萘普生酯手性识别的机理,得出溶质在固定相手性空腔中体积大小的适应性,尤其是立体结构上的空间适应性是手性识别的关键,不同的固定相这种适应性有所不同.Naproxen is a widely used profen - type nonsteriodal anti - infammatory agent. However, up to now no applications of cellulose triacetate ( CTA) or cellulose tri (4 - methylbenzoate) ( CTMB) chiral stationary phase for separating racemic naproxen or its derivatives have been reported. This paper reports successful separation of several types of racemic naproxen esters using pure polymer type CTA and CTB, coated type CTB and CTMB columns. The influence of mobile phase composition and solute structure on the chiral separation were studied. The recognition mechanism was also explored. Following are the results: ( I) hydrophobic interaction between the CSP and enantiomers plays an important role in chiral recognition for pure polymer type CTB but not so important for pure polymer type CTA; (2) for coated type. CTB, changing the polar alcohol modifier from ethanol to 2 - propanol results in loss of chiral selectivity for some racemic naproxen esters, but the polar alcohol modifier does not influence the chiral selectivity of coated type CTMB; (3) the enantiomer elution order of racemic naproxen esters is the same on pure polymer CTB, coated CTB and coated CTMB columns, but is inversed on pure polymer type CTA; (4) for all the four types of CSPs, the steric fit of the solute in the chiral cavity is the key to the chiral recognition, but the fitness is different for different CSPs.

关 键 词：液相色谱 萘普生 手性固定相 手性识别机理 分离 解热镇痛药物 纤维素衍生物 

分 类 号：R971.1[医药卫生—药品] O657.72[医药卫生—药学]