Pawlowska M, Zukowski J, Armstrong D W
University of Missouri-Rolla 65401.
J Chromatogr A. 1994 Apr 22;666(1-2):485-91. doi: 10.1016/0021-9673(94)80410-9.
New pre-column derivatizing reagents: phthalic anhydride, 3-nitrophthalic anhydride, diphenic anhydride, 1,8-naphthalic anhydride and diphenylmaleic anhydride have been developed for resolving chiral compounds having amine groups. Although all of these agents produce derivatives with high molar absorptivities, the later two also fluoresce. Upon derivatization, aromatic analytes containing free carboxylic groups are produced. Both of these moieties enhance chiral recognition on cyclodextrin-based columns. The derivatization reaction is carried out at room temperature by shaking a buffered aqueous solution of a sample with an acetonitrile solution of the reagent. The reaction is fast and proceeds without any detectable racemization. The labeled compounds have favorable chromatographic properties which are demonstrated by resolution of a number of chiral compounds on cyclodextrin-bonded phases operated with non-aqueous polar organic eluents. The selectivity and good efficiency of this system contributes to its high sensitivity and in its applicability for detecting low levels of enantiomeric impurities. The detection limit is in the picomole range and less than 0.1% enantiomeric impurities can be determined in some cases.
邻苯二甲酸酐、3-硝基邻苯二甲酸酐、联苯二甲酸酐、1,8-萘二甲酸酐和二苯基马来酸酐，用于拆分含胺基的手性化合物。尽管所有这些试剂都能产生具有高摩尔吸光率的衍生物，但后两种还会发出荧光。衍生化后，会生成含有游离羧基的芳香族分析物。这两个部分都增强了基于环糊精的色谱柱上的手性识别。衍生化反应在室温下进行，将样品的缓冲水溶液与试剂的乙腈溶液振荡混合。反应迅速且进行过程中没有任何可检测到的消旋化现象。标记的化合物具有良好的色谱性能，这通过在使用非水极性有机洗脱剂的环糊精键合相上拆分多种手性化合物得到了证明。该系统的选择性和良好效率使其具有高灵敏度，并适用于检测低水平的对映体杂质。检测限在皮摩尔范围内，在某些情况下可以测定小于0.1%的对映体杂质。
