Rizvi Syed Asad Ali, Shamsi Shahab A
Department of Chemistry, Center of Biotechnology and Drug Design, Georgia State University, Atlanta, GA 30303, USA.
Electrophoresis. 2007 Jun;28(11):1762-78. doi: 10.1002/elps.200600483.
In this work, six amino acid derived (L-leucinol, L-leucine, L-isoleucinol, L-isoleucine, L-valinol, and L-valine) polymeric chiral surfactants with carboxylate and sulfate head groups that were recently synthesized in our laboratory [30, 33, 35] are compared for the simultaneous enantioseparation of several groups of structurally similar analytes under neutral and basic pH conditions. The physicochemical properties of the monomers and polymers of both classes of sulfated and carboxylated surfactants are compared. In addition, cryogenic high-resolution electron microscopy showed tubular structures with distinct order of the tubes of 50-100 nm width. A Plackett-Burmann experimental design is used to study the factors that influence the chiral resolution and analysis time of ten structurally related phenylethylamines (PEAs). It is observed that increasing the number of hydroxy groups on the benzene ring of the PEAs resulted in deterioration of enantioseparation using any of the six polymeric surfactants. For all three classes of PEAs, polysodium N-undecenoxycarbonyl-L-amino acidate (poly-L-SUCAA)-type surfactants provided enhanced resolution compared to that of polysodium N-undecenoxycarbonyl-L-amino acid sulfates (poly-L-SUCAASS). Several classes of basic and neutral chiral compounds (e.g., beta-blockers benzoin derivatives, PTH-amino acids, and benzodiazepines) also provided improved chiral separations with poly-L-SUCAA. Among the poly-L-SUCAAs, polysodium N-undecenoxycarbonyl-L-isoleucine sulfate (poly--SUCL) exhibited overall the best enantioseparation capability for the investigated basic and neutral compounds, while among the poly-L-SUCAASs, polysodium N-undecenoxycarbonyl-L-isoleucine sulfate (poly-L-SUCILS), and polysodium N-undecenoxycarbonyl-L-valine sulfate (poly-L-SUCVS) proved to be equally effective for enantioseparation. This work clearly demonstrates that variation in the head group of polymeric alkenoxy amino acid surfactants has a significant effect on chiral separations.
在本研究中，我们比较了最近在我们实验室合成的六种氨基酸衍生的（L-亮氨醇、L-亮氨酸、L-异亮氨醇、L-异亮氨酸、L-缬氨醇和L-缬氨酸）带有羧酸盐和硫酸盐头基的聚合手性表面活性剂，用于在中性和碱性pH条件下同时对几组结构相似的分析物进行对映体分离。比较了硫酸化和羧化两类表面活性剂的单体和聚合物的物理化学性质。此外，低温高分辨率电子显微镜显示出宽度为50-100nm的具有明显有序排列的管状结构。采用Plackett-Burmann实验设计来研究影响十种结构相关苯乙胺（PEA）对映体拆分和分析时间的因素。观察到，增加PEA苯环上的羟基数量会导致使用六种聚合表面活性剂中的任何一种进行对映体分离的效果变差。对于所有三类PEA，与N-十一碳烯氧基羰基-L-氨基酸硫酸盐（聚-L-SUCAASS）相比，N-十一碳烯氧基羰基-L-氨基酸盐（聚-L-SUCAA）型表面活性剂提供了更高的拆分效率。几类碱性和中性手性化合物（如β-阻滞剂、安息香衍生物、PTH-氨基酸和苯二氮卓类）使用聚-L-SUCAA也能实现更好的手性分离。在聚-L-SUCAA中，N-十一碳烯氧基羰基-L-异亮氨酸硫酸盐（聚-L-SUCL）对所研究的碱性和中性化合物总体上表现出最佳的对映体分离能力，而在聚-L-SUCAAS中，N-十一碳烯氧基羰基-L-异亮氨酸硫酸盐（聚-L-SUCILS）和N-十一碳烯氧基羰基-L-缬氨酸硫酸盐（聚-L-SUCVS）被证明在对映体分离方面同样有效。这项工作清楚地表明，聚合链烯氧基氨基酸表面活性剂头基的变化对手性分离有显著影响。
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