Polysodium N-undecanoyl-L-leucylvalinate:: A versatile chiral selector for micellar electrokinetic chromatography
Polysodium N-undecanoyl-L-leucylvalinate:: A versatile chiral selector for micellar electrokinetic chromatography
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DOI：
10.1021/ac020386r
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发表时间：
2003-02-01
影响因子：
7.4
通讯作者：
Warner, IM
中科院分区：
文献类型：
--
作者：
Shamsi, SA;Valle, BC;Warner, IM
二肽胶束聚合物是一类新型聚合物表面活性剂，其中十一酰基-L-亮氨酰缬氨酸聚钠（聚-L-SULV）被发现是一种广泛适用于胶束电动色谱的手性选择剂。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。在广泛的手性筛选计划中，使用聚-L-SULV 作为手性假固定相，在中性 pH 值和碱性 pH 背景电解质中测试了 75 种外消旋化合物的对映体分离。选择适当浓度的聚-L-SULV 后，75 种外消旋化合物中总共有 58 种可以得到分离。尽管使用聚-L-SULV 很难拆分阴离子手性分析物，但阳离子 (77%) 和中性 (85%) 外消旋体的手性拆分成功率非常高。讨论了这种二肽胶束聚合物与各类手性分析物的静电、空间、疏水和氢键相互作用的方面。
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.