Polysodium N-undecanoyl-L-leucylvalinate: a versatile chiral selector for micellar electrokinetic chromatography |
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Authors: | Shamsi Shahab A Valle Bertha C Billiot Fereshteh Warner Isiah M |
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Affiliation: | Department of Chemistry, Center of BioTechnology and Drug Design, Georgia State University, Atlanta, Georgia 30303, USA. |
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Abstract: | 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. |
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