Shamsi Shahab A, Valle Bertha C, Billiot Fereshteh, Warner Isiah M
Department of Chemistry, Center of BioTechnology and Drug Design, Georgia State University, Atlanta, Georgia 30303, USA.
Anal Chem. 2003 Feb 1;75(3):379-87. doi: 10.1021/ac020386r.
Dipeptide micelle polymers are a new class of polymeric surfactants of which the polysodium undecanoyl-L-leucylvalinate (poly-L-SULV) was found to be a broadly applicable chiral selector for micellar electrokinetic chromatography. This negatively charged dipeptide micelle polymer is a high molecular weight compound with large countercurrent mobility, zero critical micelle concentration, low aggregation number, and high solubility in water or water-organic solvents. In an extensive chiral screening program, enantioseparation of 75 racemic compounds was tested with poly-L-SULV as chiral pseudostationary phase in neutral pH and basic pH background electrolytes. A total of 58 out of 75 racemic compounds could be resolved after choosing an appropriate concentration of poly-L-SULV. Although anionic chiral analytes are difficult to resolve using poly-L-SULV, the percent success rate for chiral resolution of cationic (77%) and neutral (85%) racemates was very high. Aspects regarding electrostatic, steric, hydrophobic, and hydrogen-bonding interactions of this dipeptide micelle polymer with various classes of chiral analytes are discussed.
二肽胶束聚合物是一类新型的聚合物表面活性剂，其中十一烷酰-L-亮氨酰缬氨酸钠（聚-L-SULV）被发现是胶束电动色谱中一种广泛适用的手性选择剂。这种带负电荷的二肽胶束聚合物是一种高分子量化合物，具有较大的逆流迁移率、零临界胶束浓度、低聚集数以及在水或水-有机溶剂中的高溶解度。在一项广泛的手性筛选实验中，以聚-L-SULV作为手性假固定相，在中性pH和碱性pH背景电解质中测试了75种外消旋化合物的对映体分离。在选择了合适浓度的聚-L-SULV后，75种外消旋化合物中共有58种能够实现分离。尽管使用聚-L-SULV难以分离阴离子手性分析物，但阳离子（77%）和中性（85%）外消旋体的手性拆分成功率非常高。本文讨论了这种二肽胶束聚合物与各类手性分析物之间的静电、空间、疏水和氢键相互作用。
