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Supercritical fluid chromatography versus high performance liquid chromatography for enantiomeric and diastereoisomeric separations on coated polysaccharides-based stationary phases: Application to dihydropyridone derivatives
Journal of Chromatography A ( IF 3.8 ) Pub Date : 2018-03-19 , DOI: 10.1016/j.chroma.2018.03.035
Vanessa Hoguet , Julie Charton , Paul-Emile Hecquet , Chahinaze Lakhmi , Emmanuelle Lipka

For analytical applications, SFC has always remained in the shadow of LC. Analytical enantioseparation of eight dihydropyridone derivatives, was run in both High Performance Liquid Chromatography and Supercritical Fluid Chromatography. Four polysaccharide based chiral stationary phases namely amylose and cellulose tris(3, 5-dimethylphenylcarbamate), amylose tris((S)-α-phenylethylcarbamate) and cellulose tris(4-methylbenzoate) with four mobile phases consisted of either n-hexane/ethanol or propan-2-ol (80:20 v:v) or carbon dioxide/ethanol or propan-2-ol (80:20 v:v) mixtures were investigated under same operatory conditions (temperature and flow-rate). The elution strength, enantioselectivity and resolution were compared in the two methodologies. For these compounds, for most of the conditions, HPLC afforded shorter retention times and a higher resolution than SFC. HPLC appears particularly suitable for the separation of the compounds bearing two chiral centers. For instance compound 7 was baseline resolved on OD-H CSP under n-Hex/EtOH 80/20, with resolution values equal to 2.98, 1.55, 4.52, between the four stereoisomers in less than 17 min, whereas in SFC, this latter is not fully separated in 23 min under similar eluting conditions. After analytical screenings, the best conditions were transposed to semi-preparative scale.



中文翻译:

超临界流体色谱高效液相色谱在基于多糖的固定相上对映异构体和非对映异构体的分离:对二氢吡啶酮衍生物的应用

对于分析应用,SFC始终处于LC的阴影之下。八种二氢吡啶酮衍生物的分析对映体分离是在高效液相色谱和超临界流体色谱中进行的。四个基于多糖的手性固定相,即直链淀粉和纤维素三(3,5-二甲基苯基氨基甲酸酯),直链淀粉三((S)-α-苯基乙基氨基甲酸酯)和纤维素三(4-甲基苯甲酸酯),其中四个流动相均由n在相同的操作条件下(温度和流速)研究了-己烷/乙醇或丙-2-醇(80:20 v:v)或二氧化碳/乙醇或丙-2-醇(80:20 v:v)混合物)。在两种方法中比较了洗脱强度,对映选择性和分离度。对于这些化合物,在大多数条件下,HPLC均比SFC提供了更短的保留时间和更高的分离度。HPLC似乎特别适合分离带有两个手性中心的化合物。例如,化合物7在OD-H CSP上于n-Hex / EtOH 80/20,在不到17分钟的时间内,四个立体异构体之间的分离度值分别等于2.98、1.55、4.52,而在SFC中,后者在相似的洗脱条件下在23分钟内未完全分离。经过分析筛选后,将最佳条件转入半制备规模。

更新日期:2018-03-19
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