Use of chiral zwitterionic surfactants for enantiomeric resolutions by capillary electrophoresis.
The enantiomeric resolution of 1,1'-binaphthyl-2,2'-diamine and Tröger's base was investigated using the commercially available zwitterionic surfactants 3-[(3-cholamidopropyl)dimethylammonio]-1-propanesulphonate (CHAPS) and 3-[(3-cholamidopropyl)dimethylammonio]-2-hydroxy-1-propanesulphonate (CHAPSO). Resolution of the weakly basic chiral probes was achieved using varying concentrations of surfactant, above their critical micellar concentrations, in a phosphate buffer (pH 2.5; 100 mM) to ensure ionisation of the analytes. Both CHAPS and CHAPSO were employed in the absence of additional coselectors or surfactants as sole micellar-forming agents. The addition of organic modifiers, methanol and acetonitrile (ACN), to the background electrolyte (BGE) was found to have a detrimental effect on enantioselectivity presumably by alteration of the phase polarity.
Hadley
Mark R
MR
Analytical Chemistry Group, Process R&D, AstraZeneca, Charter Way, Silk Road Business Park, Macclesfield, Cheshire SK10 2NA, UK. mark.hadley@astrazeneca.com
Harrison
Mark W
MW
Hutt
Andrew J
AJ
D002793:Cholic Acids; D020374:Chromatography, Micellar Electrokinetic Capillary / Q000379:methods; D019075:Electrophoresis, Capillary / Q000379:methods*; D007477:Ions; D008823:Micelles; D015394:Molecular Structure; D009281:Naphthalenes / Q000302:isolation & purification; D013237:Stereoisomerism; D013501:Surface-Active Agents / Q000737:chemistry*
C406943:BINAP, 2-naphthol; D002793:Cholic Acids; D007477:Ions; D008823:Micelles; D009281:Naphthalenes; D013501:Surface-Active Agents; C048531:chapso; C028213:3-((3-cholamidopropyl)dimethylammonium)-1-propanesulfonate