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Polysodium N-undecanoyl-L-leucylvalinate: a versatile chiral selector for micellar electrokinetic chromatography.
Analytical Chemistry ( IF 6.7 ) Pub Date : 2003 Feb 1
Shamsi, Shahab A, Valle, Bertha C, Billiot, Fereshteh, Warner, Isiah M

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.

中文翻译:

N-十一烷酰基-L-亮氨酰缬氨酸钠盐:用于胶束电动色谱的通用手性选择剂。

二肽胶束聚合物是一类新型的聚合物表面活性剂,发现十一碳酰-L-亮氨酰缬氨酸多钠盐(poly-L-SULV)是胶束电动色谱法中广泛应用的手性选择剂。该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,低聚集数和在水或水-有机溶剂中的高溶解度。在广泛的手性筛选程序中,使用聚L-SULV作为中性pH和碱性pH背景电解质中的手性假固定相,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,可以拆分出75种外消旋化合物中的58种。尽管使用聚-L-SULV难以解析阴离子手性分析物,但阳离子(77%)和中性(85%)外消旋物的手性拆分成功率非常高。讨论了有关该二肽胶束聚合物与各种手性分析物的静电,空间,疏水和氢键相互作用的方面。
更新日期:2017-01-31
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