Resolution of enantiomeric amides on a Pirkle-type chiral stationary phase. A comparison of subcritical fluid and liquid chromatographic approaches.
Resolution of enantiomeric amides on a Pirkle-type chiral stationary phase. A comparison of subcritical fluid and liquid chromatographic approaches.
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在 Pirkle 型手性固定相上拆分对映体酰胺。
DOI：
10.1016/s0021-9673(01)94704-1
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发表时间：
1986
期刊：
影响因子：
--
通讯作者：
I. Wainer
中科院分区：
文献类型：
--
作者：
P. Macaudiere;A. Tambuté;M. Caude;R. Rosset;M. A. Alembik;I. Wainer
评价了亚临界和超临界流体色层(SubFC和SFC)对一系列对映体酰胺的拆分。溶质是从2-氨基丁烷到2-氨基辛烷的一系列同系胺的2-萘甲酰胺，以及2-氨基庚烷的对甲基、对甲氧基和对氯苯酰胺。手性固定相(CSP)是(R)-N-(3，5-二硝基苯甲酰基)苯甘氨酸的共价形式。色谱柱为正己烷-异丙醇-乙腈(97：3：0.5)，流速为2ml/min，柱温为20~35℃，流动相为二氧化碳和各种极性改性剂的混合物，如醇、氯仿和水。在最佳的LC条件下，手性拆分率α由2-氨基丁烷酰胺的α=1.03增加到2-氨基辛烷酰胺的α=1.11。2-氨基庚烷(对甲基和对甲氧基)的α值大于π-酸性酰胺(对氯)的值，即π=1.08比1.04。LC和SubFC得到的选择性、分辨率和效率相似。这些结果表明，手性识别的机理在LC和SubFC中是相同的，方法应该是一成不变的。SubFC的实际分析时间比LC所需的时间要短得多：2-氨基辛酰胺的分析时间只有2分钟，而在最佳条件下，LC的分析时间超过10分钟。
Subcritical and supercritical fluid chromatography (SubFC and SFC) have been evaluated for the resolution of an homologous series enantiomeric amides. the solutes were the 2-naphthoyl amides of an homologous series of amines, ranging from 2-aminobutane to 2-aminooctane, and thep-methyl-,p-methoxy- andp-chlorophenylamide of 2-aminoheptane. The chiral stationary phase (CSP) used was the covalent form of (R)-N-(3,5-dinitrobenzoyl)phenylgylcine. In liquid chromatography (LC) the mobile phase comprised hexane-2-propanol-acetonitrile (97:3:0.5) at a flow-rate of 2ml/min and temperatures of 20–35°C. In SFC, the mobile phases were various mixtures of carbon dioxide and polar modifiers, such as alcohols, chloroform and water. For the best conditions in LC, the chiral resolution, α, increased through the homologuos series from α = 1.03 for the amide derived from 2-aminobutane to α = 1.11 for the 2-aminooctane amide. The values of α observed for the π-basic amids of 2-aminoheptane(p-methyl andp-methoxy) were greater than that observed for the π-acidic amide (p-chloro),i.e., α = 1.08versus1.04. The selectives, resolutions and efficiencies obtained by LC and SubFC were similar. These results indicate that the mechanism of chiral recognition is the same in LC and SubFC and that the methods should be inerchangeable. The actual analysis time for SubFC was significantly shorter than that required for LC: as short as 2 min for the 2-aminooctane amide, whereas LC takes over 10 min under the best conditions.