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Molecular recognition by chiral cationic micellar and micelle‐like aggregates in electrokinetic capillary chromatography
Author(s) -
Dobashi Akira,
Hamada Masaki,
Yamaguchi Junko
Publication year - 2001
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/1522-2683(200101)22:1<88::aid-elps88>3.0.co;2-u
Subject(s) - micellar electrokinetic chromatography , micelle , chemistry , pulmonary surfactant , cationic polymerization , bromide , enantiomer , hydrogen bond , chromatography , organic chemistry , isopropyl , micellar liquid chromatography , dissociation (chemistry) , polymer chemistry , capillary electrophoresis , aqueous solution , molecule , biochemistry
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.