Sousa Emília P, Tiritan M E, Oliveira Regina V, Afonso C M M, Cass Q B, Pinto Madalena M M
Centro de Estudos de Química Orgânica, Fitoquímica e Farmacologia-Universidade do Porto, Faculdade de Farmácia, Porto, Portugal.
Chirality. 2004 May 15;16(5):279-85. doi: 10.1002/chir.20031.
Analytical HPLC methods using carbamate chiral stationary phases of polysaccharide derivatives were developed for the enantiomeric resolution of five racemic mixtures of xanthonolignoids: rac-trans-kielcorin C, rac-cis-kielcorin C, rac-trans-kielcorin D, rac-trans-isokielcorin D, and rac-trans-kielcorin E. The separations were evaluated with the stationary phases cellulose tris-3,5-dimethylphenylcarbamate, amylose tris-3,5-dimethylphenylcarbamate, amylose tris-(S)-1-phenylethylcarbamate, and amylose tris-3,5-dimethoxyphenylcarbamate under normal, reversed-phase, and polar organic elution conditions. Chiral recognition of those chiral stationary phases, the influence of mobile phases on the enantiomers separation, and the effects of structural features of the solutes on the chiral discrimination observed are discussed. The best performance was achieved on an amylose tris-3,5-dimethylphenylcarbamate phase. Polar organic conditions gave shorter retention factors and better resolutions and were a valuable alternative to the alcohol-hexane or reversed-phase conditions.
采用多糖衍生物氨基甲酸酯类手性固定相的高效液相色谱分析方法，用于分离五种呫吨木脂素外消旋混合物：外消旋反式基尔考林C、外消旋顺式基尔考林C、外消旋反式基尔考林D、外消旋反式异基尔考林D和外消旋反式基尔考林E。使用三（3,5-二甲基苯基）氨基甲酸纤维素酯、三（3,5-二甲基苯基）氨基甲酸直链淀粉酯、三（S）-1-苯基乙基氨基甲酸直链淀粉酯和三（3,5-二甲氧基苯基）氨基甲酸直链淀粉酯等固定相，在正相、反相和极性有机洗脱条件下进行分离评估。讨论了这些手性固定相的手性识别、流动相对对映体分离的影响以及溶质结构特征对观察到的手性识别的影响。在三（3,5-二甲基苯基）氨基甲酸直链淀粉酯固定相上获得了最佳分离效果。极性有机条件下保留因子更短，分离度更好，是醇-己烷或反相条件的一个有价值的替代方法。
