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首页> 外文学位 >The chiral separation of albuterol derivatives with camphorsulfonic acid using LiChrosorb Diol and amylose chiral AD columns.
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The chiral separation of albuterol derivatives with camphorsulfonic acid using LiChrosorb Diol and amylose chiral AD columns.

机译：使用LiChrosorb Diol和直链淀粉手性AD色谱柱与樟脑磺酸手性分离沙丁胺醇衍生物。

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摘要

This research deals with the separation of enantiomers of aminoalcohol compounds in the ion-pair chromatographic system. Separations based on formation of diastereomeric ion pairs were applied in systems with an organic mobile phase using achiral and chiral stationary phases. In this study, (+)-10-camphor-sulfonic acid (CSA) was chosen to serve as a chiral counter ion for the separation of enantiomers of albuterol (alpha-[(tert-butylamino)methyl]-4-hydroxy-m-xylene-alpha,alpha '-diol) and related compounds, monomethyl albuterol (MMEA), monoethyl albuterol (MEEA), Over-reduced Albuterol (ORAlb), Albuterol aldehyde (AA), and Benzyl Albuterol (BA). UV spectrum of each compound in a hexane-ethanol solvent mixture with and without addition of CSA was collected and spectral details were investigated. The binding constants of albuterol and related compounds with (+)-10-camphor-sulfonic acid were determined using the phase solubility technique. The experimental results indicated that Alb, MMEA, MEEA, AA, ORAlb, and BA formed fairly strong complexes with CSA. These conclusions were in fair agreement with the results obtained from chromatographic experiments. The substituent groups not only differentiated the binding powers between alcohol amines and CSA, but also influenced the complexing ability between two enantiomers with stationary phases. The effect is significant and is counted for the diastereomeric separation.; The chiral separation of albuterol and related compounds was initially performed with an achiral column, LiChrosorb Diol using the CSA chiral selector in hexane-ethanol mobile phase. In order to regulate retention and stereoselectivity, the effect of factors on the retention time and resolution including concentration of the chiral selector, the polar alcohol content in the mobile phase, and the column temperature was studied. Several parameters such as separation factor (alpha), resolution (Rs), and retention factor (k') were evaluated in order to achieve the enantiomeric separation and to define optimal conditions. With a mobile phase consisting of hexane, ethanol, triethylamine, and the complexing reagent, camphorsulfonic acid (CSA), Alb, MMEA, and MEEA were baseline resolved with the concentration of CSA at 0.01 N or greater; whereas ORAlb were only separated if the CSA concentration was below 0.02 N. AA and BA were not separated under any experimental condition explored using the LiChrosorb Diol column.; The enantioseparations of albuterols using the chiral stationary phase (CSP) of amylose tris(3,5-dimethylphenyl-carbamate), Chiralpak AD, was also investigated with and without an addition CSA in the mobile phase. In the absence of CSA, each enantiomer eluted at different retention time. However only Alb, MMEA, MEEA, and ORAlb were baseline resolved. AA and BA were partially separated using the similar mobile phase system. In the presence of CSA, the separation of two enantiomers was improved and the increase of the enantioselectivity of albuterols averaged about 20 percent. This study demonstrated interest and advantage in using a chiral stationary phase in combination of a chiral additive in the mobile phase to enhance the chiral separation.
机译：该研究涉及离子对色谱系统中氨基醇化合物对映体的分离。基于非对映体离子对形成的分离已应用于使用非手性和手性固定相的有机流动相系统中。在这项研究中，选择（+）-10-樟脑磺酸（CSA）作为手性抗衡离子，用于分离沙丁胺醇（α-[[（叔丁基氨基）甲基] -4-羟基-m -二甲苯-α，α'-二醇）和相关化合物，单甲基沙丁胺醇（MMEA），单乙基沙丁胺醇（MEEA），过度还原的丁烯醇（ORAlb），丁烯醇醛（AA）和苄基丁烯醇（BA）。收集添加和不添加CSA的己烷-乙醇溶剂混合物中每种化合物的UV光谱，并研究光谱细节。使用相溶解度技术确定沙丁胺醇和相关化合物与（+）-10-樟脑磺酸的结合常数。实验结果表明，Alb，MMEA，MEEA，AA，ORAlb和BA与CSA形成了很强的配合物。这些结论与色谱实验的结果完全吻合。取代基不仅可以区分醇胺和CSA之间的结合力，而且可以影响具有固定相的两种对映异构体之间的络合能力。该作用是显着的，并计入非对映异构体分离中。沙丁胺醇和相关化合物的手性分离最初是使用CSA手性选择剂在己烷-乙醇流动相中使用非手性色谱柱LiChrosorb Diol进行的。为了调节保留和立体选择性，研究了影响保留时间和分离度的因素，包括手性选择剂的浓度，流动相中的极性醇含量和柱温。为了实现对映异构体分离和定义最佳条件，对几个参数进行了评估，例如分离因子（α），分离度（Rs）和保留因子（k'）。使用由己烷，乙醇，三乙胺和络合剂组成的流动相，以0.01 N或更高的浓度对樟脑磺酸（CSA），Alb，MMEA和MEEA进行基线分离；然而，仅当CSA浓度低于0.02 N时才分离ORAlb。在使用LiChrosorb Diol色谱柱探索的任何实验条件下，AA和BA均未分离。还研究了使用直链淀粉三（3,5-二甲基苯基氨基甲酸酯）手性固定相（CSP），Chiralpak AD对沙丁胺醇的对映体分离，在流动相中添加或不添加CSA的情况。在没有CSA的情况下，每种对映异构体在不同的保留时间洗脱。但是，只有Alb，MMEA，MEEA和ORAlb可以通过基线解决。使用相似的流动相系统将AA和BA部分分离。在CSA的存在下，两种对映异构体的分离得到了改善，沙丁胺醇的对映选择性平均提高了约20％。这项研究证明了在流动相中使用手性固定相与手性添加剂的组合以增强手性分离的兴趣和优势。

著录项

  • 作者

    Li, Hui.;

  • 作者单位

    University of Massachusetts Lowell.;

  • 授予单位 University of Massachusetts Lowell.;
  • 学科 Chemistry Analytical.
  • 学位 Ph.D.
  • 年度 2004
  • 页码 169 p.
  • 总页数 169
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 化学;
  • 关键词

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