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化学学报
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化学学报 ›› 2001, Vol. 59 ›› Issue (11): 1975-1981. 上一篇    下一篇

研究论文

N-苄氧甲酰基-α-氨基膦酸二苯酯有机磷化合物高效液相 色谱保留和手性识别 机理的研究

黄君珉;陈慧;王琴孙;高如瑜;陈茹玉   

  1. 南开大学元素有机化学研究所.天津(300071)
  • 发布日期:2001-11-15

Study on retention and chiral recognition mechanisms of diphenyl 1- (N-benzyloxycarbonyl)-aminoalkanephosphonates organophosphorus compounds in HPLC

Huang Junmin;Chen Hui;Wang Qinsun;Gao Ruyu;Chen Ruyu   

  1. Nankai Univ, Elementoorgan Chem Lab.Tianjin(300071)
  • Published:2001-11-15

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639

被引次数

6 | 3

在正相条件下，首次对一系列N-苄氧甲酰基-α-氨基膦酸二苯酯化合物在环糊精类固定相CYCLOBONDISN和Pirkle型固定相SumichiralOA4700上实现了高效液相色谱手性折分，探索运用定量结构-对映异构体选择性保留关系的方法，将对映异构体的色谱保留和溶质分子描述参数相关性联系建立定量方程，结比研究了这二种不同类型的手性固定相对该系列有机磷化合物的色谱保留和手性识别机理，结果表明：对该系列化合物而言，Pirkle型手性因定相SumichiralOA4700的色谱手性折分能力明显优于在β-环糊精上衍生引入了额外的与前者类同的Pirkle型不对称中心的环糊精类固定相CYCLOBONDISN;环糊精类固定相CYCLOBONDISN在正相色谱条件下，包结机理不起主要作用，其作用方式更接近"Pirkle"型手性固定相；虽然二者具有类同的Pirkle型不对称中心，但是，手性识别机理差异显著，在CYCLOBONDISN手性固定相上，对N-苄氧甲酰基-α-氨基膦酸二苯酯化合物色谱折分贡献较大的是其logP和Angle参数相应的相互作用，环糊精提供的不对称性环境对手性识别有重要影响；而SumichiralOA4700对该系列化合物的手性识别与locD和TE相应的作用力相关。

关键词: 膦酸酯类, 有机磷化合物, 高速液体色谱, 固定相, 手性识别, 异构体, 选择性

Under normal phase condition, the enantiomers of a series of diphenyl 1-(N-benzyloxycarbonly)-aminoalkanephosphonates have first been separated on the two commercial chiral stationary phases of cyclodextrin- typed CYCLOBOND I SN and Pirkle-typed Sumichiral OA 4700 by high performance liquid chromatography. In order to study the retention and chiral recognition mechanism, the method of quantitative structure- enantioselectivity retention relationships was investigated from the quantitative equations established between the chromatographic retention of enantiomers and their molecular descriptors of physico-chemical properties. The mathematical statistical method is the multiple stepwise regression analysis in which the optimized equation can be obtained by choosing and deleting proper parameters according to the mathematical significant test. The results show the on the two commercial chiral stationary phases, the organophosphorus compounds of diphenyl 1-(N-benzyloxycarbonyl)- aminoalkanephosphonates have different retention and chiral recognition mechanism although the two commercial chiral stationary phases have the same Pirkle-typed chiral group and under the normal phase condition. On the chiral stationary phases of cyclodextrin- typed CYCLOBOND I SN, it is the parameters of logP and Angle that give the most contribution to the chromatographic chiral separation of diphenyl 1-(N-benzyloxycarbonyl)- aminoalkanephosphonates. Nevertheless, it is the contribution of the parameters of locD and TE that forms the chiral recognition on the chiral stationary phases of Pirkle-typed Sumichiral OA 4700 about these organophosphorus compounds.

Key words: PHOSPHONIC ACID ESTER, ORGANO PHOSPHORUS COMPOUNDS, HIGH SPEED LIQUID CHROMATOGRAPHY, STATIONARY PHASE, ISOMER, SELECTIVITY

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