Enantioselective Liquid-Solid Extraction (ELSE)--An Unexplored, Fast, and Precise Analytical Method.
A novel method of evaluating the enantioselectivity of chiral receptors is investigated. It involves extraction of an ionic guest in racemic form from an ion-exchange resin to the organic solvent, where it is bound by a chiral receptor. The enantioselectivity of the examined receptor is determined simply by measuring the enantiomeric excess of the extracted guest. We show that the concept is viable for neutral receptors binding chiral organic anions extracted into acetonitile. This method was determined to be more accurate and far less time-consuming than the classical titrations. Multiple racemic guests can be applied to a resin in a single experiment, giving the method a very high throughput.
Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.
Filip
F
Ulatowski
Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.
Paulina
P
Hamankiewicz
Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.
Janusz
J
Jurczak
D000465:Algorithms; D000596:Amino Acids / Q000138:chemical synthesis; D000838:Anions; D002849:Chromatography, Gas; D057166:High-Throughput Screening Assays; D007474:Ion Exchange; D007475:Ion Exchange Resins; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015203:Reproducibility of Results; D052616:Solid Phase Extraction / Q000379:methods*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000596:Amino Acids; D000838:Anions; D007475:Ion Exchange Resins
anion binding; chiral recognition; enantioselective extraction; high throughput; host−guest interactions