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Dodecyl thioglycopyranoside sulfates: Novel sugar‐based surfactants for enantiomeric separations by micellar electrokinetic capillary chromatography
Author(s) -
Tano Chiharu,
Son SangHyun,
Furukawa Junichi,
Furuike Tetsuya,
Sakairi Nobuo
Publication year - 2008
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.200800045
Subject(s) - chemistry , sodium dodecyl sulfate , micellar electrokinetic chromatography , enantiomer , pulmonary surfactant , chromatography , capillary electrophoresis , sodium , anomer , stereochemistry , organic chemistry , biochemistry
Four novel chiral anionic surfactants having carbohydrate hydrophilic heads, sodium n ‐dodecyl 1‐thio‐β‐ D ‐glucopyranoside 6‐hydrogen sulfate (6‐βGlcD), sodium n ‐dodecyl 1‐thio‐β‐ L ‐glucopyranoside 6‐hydrogen sulfate (6‐βGlcL), sodium n ‐dodecyl 1‐thio‐β‐ L ‐fucopyranoside 3‐hydrogen sulfate (3‐βFucL), and sodium n ‐dodecyl 1‐thio‐α‐ L ‐rhamnopyranoside 3‐hydrogen sulfate (3‐αRhaL), were synthesized by selective sulfation of the corresponding thioglycosides. Their CMC determined by fluorescence using pyrene as a probe in water was 1.3–2.7 mM. These surfactants found to be useful as chiral selectors for enantiomeric separation by MEKC. The enantiomeric separation was optimized with respect to pH, buffer concentration, and surfactant concentration. Under the optimized conditions (50 mM phosphate buffer at pH 6.5, 30 mM surfactant, 20 kV), the enantiomeric separations of five dansylated amino acids (Dns‐AAs) were achieved within approximately 20 min with the migration order of Val < Met < Leu < Phe < Trp. With 6‐βGlcD, all D ‐forms of Dns‐AAs were found to migrate faster than the corresponding L ‐forms, whereas the migration order of the enantiomers was completely reversed with the surfactant 6‐βGlcL having inversed absolute configuration of 6‐βGlcD. Among four surfactants examined, β‐anomers were much superior chiral selectors than α‐anomers, and the maximum resolution was obtained with the 6‐deoxy sugar, 3‐βFucL. These results indicated that the structures of the surfactant head groups including their anomeric configurations have significant effects on the enantiomeric separation and the migration behavior in MEKC.

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