Polysodium N-undecanoyl-L-leucylvalinate: a versatile chiral selector for micellar electrokinetic chromatography.
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.
Shamsi
Shahab A
SA
Department of Chemistry, Center of BioTechnology and Drug Design, Georgia State University, Atlanta, Georgia 30303, USA.
Valle
Bertha C
BC
Billiot
Fereshteh
F
Warner
Isiah M
IM
D020374:Chromatography, Micellar Electrokinetic Capillary / Q000379:methods*; D004151:Dipeptides / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000302:isolation & purification*; D008823:Micelles; D013237:Stereoisomerism
D004151:Dipeptides; D006841:Hydrocarbons, Aromatic; D008823:Micelles