Separation of O- and C-allyl glycoside anomeric mixtures by capillary electrophoresis and high-performance liquid chromatography.
Rapid and reliable methods for the analysis of O- and C-allyl galactopyranosides and glucopyranosides are presented, based on capillary zone electrophoresis (CZE) and micellar electrokinetic capillary chromatography (MEKC). In MEKC, the formation of chromophoric and charged complexes between the saccharides and borate as well as the hydrophobic interactions with micelles jointly contributed to the selective separation and sensitive detection of all the investigated anomeric couples. Some non-purified synthesis mixtures of C-allyl glycosides were successfully characterised without pre-treatment. MEKC buffer conditions for which glycosides separation was successfully achieved were then exported and applied to reverse-phase liquid chromatography (RP-HPLC), for the quantitative isolation of each allyl glycoside anomer. Identification of the obtained anomeric products was performed by electrospray mass spectrometry and (13)C NMR spectroscopy. Glycoside-solvent interactions driving the selective anomeric separation were shortly addressed and discussed on the basis of sugar derivatives structural differences.
Rossi
Marco
M
Department of Biochemistry, Biophysics and Macromolecular Chemistry, University of Trieste, Via L. Giorgieri 1, I-34127 Trieste, Italy.
Campa
Cristiana
C
Gamini
Amelia
A
Coslovi
Anna
A
Donati
Ivan
I
Vetere
Amedeo
A
Paoletti
Sergio
S
D000498:Allyl Compounds / Q000737:chemistry / Q000302:isolation & purification*; D002021:Buffers; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D020374:Chromatography, Micellar Electrokinetic Capillary / Q000379:methods*; D019075:Electrophoresis, Capillary / Q000379:methods*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013997:Time Factors
D000498:Allyl Compounds; D002021:Buffers; D006027:Glycosides