SYNTHESIS AND LIQUID-CHROMATOGRAPHIC EVALUATION OF SOME CHIRAL DERIVATIZING AGENTS FOR RESOLUTION OF AMINE ENANTIOMERS

SYNTHESIS AND LIQUID-CHROMATOGRAPHIC EVALUATION OF SOME CHIRAL DERIVATIZING AGENTS FOR RESOLUTION OF AMINE ENANTIOMERS
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DOI:
10.1021/ac00270a022
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发表时间:
1984-01-01
影响因子:
7.4
通讯作者:
BARKSDALE, JM
BARKSDALE, JM
中科院分区:
化学1区
文献类型:
--
作者:
CLARK, CR;BARKSDALE, JM

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合成了一系列1-[(4-取代苯基)磺酰基]脯氨酰氯,并对其作为手性衍生化试剂用于对映体胺的高效液相色谱分析进行了评价。非对映异构体1-[(4-硝基苯基)磺酰基]丙酰胺类化合物具有很强的紫外光吸收特性,可通过正相和反相液相色谱分离。第一种是利用对映体与手性固定材料相互作用速率的差异。Kotake等人(1)报道了使用纤维素固定相拆分氨基酸对映体的方法。自从这份首次报告以来,人们在手性固定相上对映体的GC拆分进行了大量的研究,并描述了许多这样的固定相(2,3)。近年来,手性固定相液相色谱分离对映体受到了极大的关注。这些固定相包括:键合在二氧化硅(4)或葡聚糖(5)上的手性配体、手性冠醚(6)和微晶三醋酸酯纤维素(7)。
A series of 1-[(4-substituted-phenyl) sulfonyl] prolyl chlorides were synthesized and evaluated as chiral derivatizing agents for the liquid chromatographic analysis of enantiomeric amines. The diastereomeric 1-[(4-nltrophenyl) sulfonyl] prollnamldes showed strong UV absorbance properties and were separable by both normal-phase and reversed-phase liquid chromatographic techniques.The reported methods for the chromatographic resolution of enantiomers fall into three categories. The first makes use of the differences in rates of interaction of enantiomers with chiral stationary materials. Kotakeet al.(1) reported the chromatographic resolution of amino acid enantiomers uti-lizing a stationary phase of cellulose. Since this initial report much effort has been put forth instudying the GC resolution of enantiomers on chiral stationary phases and numerous such stationary phases have been described (2, 3). More recently, the liquid chromatographic separation of enantiomers on chiral stationary phases has enjoyed a great deal of attention. These stationary phases include: chiral ligands bonded to silica (4) or Sephadex (5), chiral crown ethers (6), and microcrystalline cellulose triacetate (7).