Polymeric alkenoxy amino acid surfactants: V. Comparison of carboxylate and sulfate head group polymeric surfactants for enantioseparation in MEKC
Polymeric alkenoxy amino acid surfactants: V. Comparison of carboxylate and sulfate head group polymeric surfactants for enantioseparation in MEKC
复制标题
聚合烯氧基氨基酸表面活性剂：五、羧酸盐和硫酸盐头基聚合表面活性剂在 MEKC 中对映体分离的比较
DOI：
10.1002/elps.200600483
复制
发表时间：
2007
期刊：
影响因子：
2.9
通讯作者：
S. Shamsi
中科院分区：
文献类型：
--
作者：
S. A. Rizvi;S. Shamsi
在这项工作中，我们实验室最近合成了六种氨基酸衍生的（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）聚合手性表面活性剂，这些表面活性剂具有羧酸盐和硫酸盐头基[30,33,35]，比较了在中性和碱性pH条件下几组结构相似的分析物的同时对映分离。比较了两类硫酸化和羧化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管状结构，其宽度为 50-100nm 的管具有明显的顺序。 Plackett-Burmann 实验设计用于研究影响十种结构相关的苯乙胺 (PEA) 的手性拆分和分析时间的因素。据观察，增加 PEAs 苯环上的羟基数量会导致使用六种聚合物表面活性剂中任何一种的对映分离效果恶化。对于所有三类 PEA，与 N-十一烯氧基羰基-L-氨基酸硫酸多钠（聚-L-SUCAASS）相比，N-十一烯氧基羰基-L-氨基酸多钠（聚-L-SUCAA）型表面活性剂提供了更高的分辨率。几类碱性和中性手性化合物（例如，β-阻滞剂安息香衍生物、PTH-氨基酸和苯二氮卓类）也提供了聚-L-SUCAA 改进的手性分离。在聚-L-SUCAAS中，N-十一烯氧基羰基-L-异亮氨酸硫酸钠（聚-SUCL）对所研究的碱性和中性化合物总体表现出最好的对映分离能力，而在聚-L-SUCAAS中，N-十一烯氧基羰基-L-异亮氨酸硫酸钠（聚-L-SUCILS）和N-十一烯氧基羰基-L-缬氨酸硫酸多钠(poly-L-SUCVS) 被证明对于对映体分离同样有效。这项工作清楚地表明，聚合烯氧基氨基酸表面活性剂头基的变化对手性分离具有显着影响。
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., β‐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.
GR 24 对映体：合成、NMR 光谱、X 射线晶体学和手性电动毛细管色谱分离。
影响因子：
7.4
作者：
Rugutt,JK;Yarabe,HH;Shamsi,SA;Billodeaux,DR;Fronczek,FR;Warner,IM
通讯作者：
Warner,IM
两种手性聚合物表面活性剂与模型物质苯硫内酰脲氨基酸相互作用的表征和热力学研究。
影响因子：
7.4
作者：
Yarabe,HH;Shamsi,SA;Warner,IM
通讯作者：
Warner,IM
聚合二肽表面活性剂中的氨基酸顺序：对物理性质和对映选择性的影响。
影响因子：
7.4
作者：
Billiot,E;Agbaria,RA;Thibodeaux,S;Shamsi,S;Warner,IM
通讯作者：
Warner,IM