Synthesis and analytical characterization of the sodium salt of heptakis(2-O-methyl-3,6-di-O-sulfo)cyclomaltoheptaose, a chiral resolving agent candidate for capillary electrophoresis.
A pure, single isomer, strong electrolyte chiral resolving agent candidate for capillary electrophoresis, the sodium salt of heptakis(2-O-methyl-3,6-di-O-sulfo)cyclomaltoheptaose has been synthesized on the 100-g scale, in greater than 97% purity, through heptakis(2,6-di-O-tert-butyldimethylsilyl)cyclomaltoheptaose, heptakis(2-O-methyl-3,6-di-O-tert-butyldimethylsilyl)cyclomaltohep taose and heptakis(2-O-methyl)cyclomaltoheptaose intermediates. The structural identity of each intermediate and the final product was conclusively established by high-resolution MALDI-TOF mass spectrometry, variable-temperature 1H and 13C NMR spectroscopy and X-ray crystallography. The purity of each intermediate and the final product was determined by gradient high-performance liquid chromatography (HPLC) and indirect UV detection capillary electrophoresis.
Maynard
D K
DK
Department of Chemistry, Texas A&M University, College Station 77842-3012, USA.
Vigh
G
G
D002851:Chromatography, High Pressure Liquid; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry; D019075:Electrophoresis, Capillary / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012492:Salts / Q000138:chemical synthesis*; D017670:Sodium Compounds / Q000138:chemical synthesis*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013696:Temperature; D047392:beta-Cyclodextrins
D003505:Cyclodextrins; D009844:Oligosaccharides; D012492:Salts; D017670:Sodium Compounds; D047392:beta-Cyclodextrins; C420663:heptakis(2-O-methyl-3,6-di-O-sulfo)cyclomaltoheptaose; C031215:betadex