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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
Author(s) -
Moni Lisa,
Ciogli Alessia,
D'Acquarica Ilaria,
Dondoni Alessandro,
Gasparrini Francesco,
Marra Alberto
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000106
Subject(s) - cycloaddition , chemistry , hydrophilic interaction chromatography , propargyl , silica gel , azide , monosaccharide , sugar , alkyne , click chemistry , organic chemistry , chromatography , high performance liquid chromatography , catalysis
Abstract 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.