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Polymeric alkenoxy amino acid surfactants: I. Highly selective class of molecular micelles for chiral separation of β‐blockers
Author(s) -
Rizvi Syed A. A.,
Shamsi Shahab A.
Publication year - 2003
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/elps.200305516
Subject(s) - micelle , chemistry , critical micelle concentration , polymer , amide , pulmonary surfactant , alkyl , capillary electrophoresis , polymer chemistry , micellar electrokinetic chromatography , chromatography , organic chemistry , aqueous solution , biochemistry
Two amino acid‐based alkenoxy micelle polymers were synthesized for this study. These include polysodium N ‐undecenoxy carbonyl‐ L ‐leucinate (poly‐ L ‐SUCL) and polysodium N ‐undecenoxy carbonyl‐ L ‐isoleucinate (poly‐ L ‐SUCIL). The polymerization time and concentration of the synthesized micelle polymers were optimized by 1 H‐nuclear magnetic resonance (NMR) and capillary electrophoresis (CE) experiments. Detailed physicochemical properties ( 1 H NMR, critical micelle concentration (CMC), optical rotation, partial specific volume, aggregation number, and polarity) were determined, and these molecular micelles were introduced as a pseudostationary phase in micellar electrokinetic chromatography to study the molecular recognition and to develop a method for simultaneous separation of eight chiral β‐blockers. It is found that poly‐ L ‐SUCL gives overall better chiral resolution and wider chiral window than poly‐ L ‐SUCIL. After optimizing the type of micelle polymer, injection size and temperature, simultaneous separation and enantioseparation of eight β‐blockers were achieved in less than 35 min. A comparison with the amide‐type surfactants of the same polar head group and alkyl chain length showed that carbamate‐type surfactants always work better than the corresponding amide‐type surfactant.