Billiot E, Macossay J, Thibodeaux S, Shamsi S A, Warner I M
Department of Chemistry, Louisiana State University, Baton Rouge 70803, USA.
Anal Chem. 1998 Apr 1;70(7):1375-81. doi: 10.1021/ac9709561.
Chiral separations using various polymerized dipeptide surfactants in electrokinetic capillary chromatography (EKC) are investigated. The two main dipeptide surfactants used in this study were sodium N-undecylenyl-L-valine-L-leucine (L-SUVL), and sodium N-undecylenyl-L-leucine-L-valine (L-SULV). These studies were performed in order to determine if the order of amino acids in dipeptide surfactants is important in terms of chiral recognition and separations. Both the monomer and the polymer of these two surfactants were compared for the separation of two model atropisomers, (+/-)-1,1-bi-2-naphtol (BOH) and (+/-)-1,1'-bi-2-naphthyl-2,2'-diyl hydrogen phosphate (BNP). Some advantages and disadvantages of the polymer relative to the monomer are discussed. Four other surfactants, the polymers of sodium N-undecylenyl-L-leucine-L-leucine (L-SULL), sodium N-undecylenyl-L-valine-L-valine (L-SUVV), sodium N-undecylenyl-L-valine (L-SUV), and sodium N-undecylenyl-L-leucine (L-SUL), were also used in this study, and their performance was compared to that of poly(L-SULV). These data show conclusively that the order of amino acids in dipeptide surfactants has a dramatic effect on chiral recognition. Our investigations indicate that poly-(L-SULV) provides the best enantioselectivity among the four dipeptide and two single amino acid surfactants for the separation of BNP and BOH. The advantages of poly-(L-SULV) are demonstrated via the ultrafast separation of the enantiomers of BNP and BOH in less than 1 min.
研究了在电动毛细管色谱法（EKC）中使用各种聚合二肽表面活性剂进行手性分离的情况。本研究中使用的两种主要二肽表面活性剂是N-十一碳烯酰基-L-缬氨酸-L-亮氨酸钠（L-SUVL）和N-十一碳烯酰基-L-亮氨酸-L-缬氨酸钠（L-SULV）。进行这些研究是为了确定二肽表面活性剂中氨基酸的顺序在手性识别和分离方面是否重要。比较了这两种表面活性剂的单体和聚合物对两种模型阻转异构体（+/-）-1,1'-联-2-萘酚（BOH）和（+/-）-1,1'-联-2-萘基-2,2'-二磷酸氢酯（BNP）的分离效果。讨论了聚合物相对于单体的一些优缺点。本研究还使用了其他四种表面活性剂，即N-十一碳烯酰基-L-亮氨酸-L-亮氨酸钠（L-SULL）、N-十一碳烯酰基-L-缬氨酸-L-缬氨酸钠（L-SUVV）、N-十一碳烯酰基-L-缬氨酸钠（L-SUV）和N-十一碳烯酰基-L-亮氨酸钠（L-SUL），并将它们的性能与聚（L-SULV）的性能进行了比较。这些数据确凿地表明，二肽表面活性剂中氨基酸的顺序对手性识别有显著影响。我们的研究表明，在四种二肽和两种单氨基酸表面活性剂中，聚（L-SULV）对BNP和BOH的分离具有最佳的对映体选择性。聚（L-SULV）的优势通过在不到1分钟的时间内对BNP和BOH对映体的超快速分离得到了证明。
