Synthesis and examination of sulfated cyclofructans as a novel class of chiral selectors for CE.
Cyclofructans (CFs) are a class of cyclic oligosaccharides with a crown ether skeleton. No enantioseparations have previously been reported using this class of chiral oligosaccharides in chromatography or electrophoresis. CFs and their sulfated derivatives were examined as chiral selectors using CE. The native CFs showed no enantioselectivity toward any tested compounds, while the sulfated CFs showed exceptional selectivity toward many cationic analytes, including primary, secondary, and tertiary amines and amino acids. Enantiomeric resolution factors as high as 15.4 were achieved within short analysis times (generally below 10 min). The effect of buffer type, buffer concentration, buffer pH, chiral selector concentration and organic modifier concentration was examined and optimized.
Jiang
Chunxia
C
Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019-0065, USA.
Tong
Man-Yung
MY
Breitbach
Zachary S
ZS
Armstrong
Daniel W
DW
D000588:Amines / Q000302:isolation & purification; D000596:Amino Acids / Q000302:isolation & purification; D002021:Buffers; D043844:Crown Ethers / Q000138:chemical synthesis*; D019075:Electrophoresis, Capillary / Q000379:methods*; D005630:Fructans / Q000138:chemical synthesis*; D006863:Hydrogen-Ion Concentration; D047028:Macrocyclic Compounds / Q000138:chemical synthesis; D013237:Stereoisomerism; D013463:Sulfuric Acid Esters / Q000138:chemical synthesis*
D000588:Amines; D000596:Amino Acids; D002021:Buffers; D043844:Crown Ethers; D005630:Fructans; D047028:Macrocyclic Compounds; D013463:Sulfuric Acid Esters