Synthesis of sugar-based silica gels by copper-catalysed azide-alkyne cycloaddition via a single-step azido-activated silica intermediate and the use of the gels in hydrophilic interaction chromatography.
Novel sugar-based silica gels were prepared by exploiting the copper-catalysed azide-alkyne cycloaddition (CuAAC) of two different sugar alkynes, namely, ethynyl C-galactoside 1 and propargyl O-lactoside 2, with new single-step azido-activated silica gels. The fully characterised stationary phases were generally used for hydrophilic interaction chromatography (HILIC), with particular application in the stereoselective separation of monosaccharides. Dynamic HILIC (DHILIC) experiments were performed to evaluate the influence of mutarotation on the chromatographic peak shapes of two interconverting sugar anomers. The potential of such materials was shown in the separation of other highly polar compounds, including amino acids and flavonoids.
Moni
Lisa
L
Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, 44100 Ferrara, Italy.
Ciogli
Alessia
A
D'Acquarica
Ilaria
I
Dondoni
Alessandro
A
Gasparrini
Francesco
F
Marra
Alberto
A
D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D002845:Chromatography; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D005697:Galactosides / Q000138:chemical synthesis* / Q000737:chemistry; D005782:Gels / Q000138:chemical synthesis* / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012822:Silicon Dioxide / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D001386:Azides; D005697:Galactosides; D005782:Gels; D009005:Monosaccharides; D012822:Silicon Dioxide; D003300:Copper