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

被引：59

作者：

Moni, Lisa ^{[2
]}

Ciogli, Alessia ^{[1
]}

D'Acquarica, Ilaria ^{[1
]}

Dondoni, Alessandro ^{[2
]}

Gasparrini, Francesco ^{[1
]}

Marra, Alberto ^{[2
]}

机构：

[1] Univ Roma La Sapienza, Dipartimento Chim & Tecnol Farm, I-00185 Rome, Italy

[2] Univ Ferrara, Dipartimento Chim, Chim Organ Lab, I-44100 Ferrara, Italy

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 19期

关键词：

azides; click chemistry; liquid chromatography; silica gels; sugar anomers; PERFORMANCE LIQUID-CHROMATOGRAPHY; LIGHT-SCATTERING DETECTION; ELECTROSPRAY MASS-SPECTROMETRY; CYCLODEXTRIN-BONDED PHASE; CLICK-CHEMISTRY; POLAR COMPOUNDS; MAGNETIC NANOPARTICLE; STATIONARY PHASES; FAST EQUILIBRIUM; REDUCING SUGARS;

D O I：

10.1002/chem.201000106

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：5712 / 5722

页数：11

共 56 条

[51] Hydrophilic interaction chromatography electrospray mass spectrometry analysis of polar compounds for natural product drug discovery [J].

Strege, MA .

ANALYTICAL CHEMISTRY, 1998, 70 (13) :2439-2445

[52] Investigation on enantiomeric separations of fluorenylmethoxycarbonyl amino acids and peptides by high-performance liquid chromatography using native cyclodextrins as chiral stationary phases [J].

Tang, Y ;

Zukowski, J ;

Armstrong, DW .

JOURNAL OF CHROMATOGRAPHY A, 1996, 743 (02) :261-271

[53] Analysis of highly polar compounds of plant origin: Combination of hydrophilic interaction chromatography and electrospray ion trap mass spectrometry [J].

Tolstikov, VV ;

Fiehn, O .

ANALYTICAL BIOCHEMISTRY, 2002, 301 (02) :298-307

[54] Methods of analysis and separation of chiral flavonoids [J].

Yanez, Jaime A. ;

Andrews, Preston K. ;

Davies, Neal M. .

JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 2007, 848 (02) :159-181

[55] Hydrophilic Interaction Chromatography Based Enrichment of Glycopeptides by Using Click Maltose: A Matrix with High Selectivity and Glycosylation Heterogeneity Coverage [J].

Yu, Long ;

Li, Xiuling ;

Guo, Zhimou ;

Zhang, Xiuli ;

Liang, Xinmiao .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (46) :12618-12626

[56] HILIC for separation of co-eluted flavonoids under RP-HPLC mode [J].

Zhang, Hui ;

Guo, Zhimou ;

Zhang, Feifang ;

Xu, Qing ;

Liang, Xinmiao .

JOURNAL OF SEPARATION SCIENCE, 2008, 31 (09) :1623-1627

← 1 2 3 4 5 6 →