Molecular recognition by chiral cationic micellar and micelle-like aggregates in electrokinetic capillary chromatography.
We examined the enantiomer separation with micelles and a micelle-like polymer made with trimethylammonium-terminated surfactants all of whose hydrocarbon chains contain hydrogen bonding valinediamide moieties in electrokinetic chromatography (EKC). The surfactants used were 3-(N-dodecanoyl-L-valylamino)-propyltrimethylammonium bromide (surfactant 1) and 6-(N-nonanoyl-L-valylamino)hexyl-trimethylammonium bromide (surfactant 2); the micelle-like polymer was derived from 3-(N-10-undecenoyl-L-valyl)aminopropyltrimethylammonium bromide (surfactant 3). N-Acylamino acids and their isopropyl esters were separated with enantiomers with the same configuration as the chiral surfactant and which were retained to a greater extent than the counterparts in micelles. The micellar hydrophobic environment, in which amides function as hydrogen bonding sites with solutes, and ceased micellar kinetic association-dissociation with polymerization are discussed.
Dobashi
A
A
School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan. dobashi@ps.toyaku.ac.jp
Hamada
M
M
Yamaguchi
J
J
D000596:Amino Acids / Q000302:isolation & purification; D001965:Bromides / Q000737:chemistry; D002412:Cations; D020374:Chromatography, Micellar Electrokinetic Capillary / Q000379:methods*; D008055:Lipids; D008823:Micelles; D011108:Polymers; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013501:Surface-Active Agents / Q000737:chemistry*; D014867:Water
C423989:3-(N-10-undecenoyl-L-valyl)aminopropyl trimethylammonium bromide; C423990:3-(N-dodecanoyl-L-valylamino)-propyltrimethylammonium bromide; C423988:6-(N-nonanoyl-L-valylamino)-propyltrimethylammonium bromide; D000596:Amino Acids; D001965:Bromides; D002412:Cations; D008055:Lipids; D008823:Micelles; D011108:Polymers; D000644:Quaternary Ammonium Compounds; D013501:Surface-Active Agents; D014867:Water