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Precursor Carboxy-silica for Functionalization With Interactive Ligands. II. Carbodiimide Assisted Preparation of Silica Bonded Stationary Phases with D-glucamine for Hydrophilic Interaction Liquid Chromatography

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Abstract

A precursor carboxy-silica support was introduced for grafting a retentive polar ligand, namely D-glucamine, for use in hydrophilic interaction liquid chromatography. This support was prepared by sequentially reacting 5 µm silica particles with vinyltrimethoxysilane and then thioglycolic acid. The carboxy-silica thus obtained was subsequently functionalized with D-glucamine by on-column reactions via a carbodiimide conjugation reaction. These reactions series, which are applied for the first time in HPLC column fabrication, yielded the D-glucamide-silica column. This polar column was evaluated for its hydrophilic interaction chromatography retention properties with derivatized mono- and oligosaccharides, phenolic and benzoic acid derivatives, nucleobases, nucleosides and nucleotides. The D-glucamide-silica column exhibited a good selectivity towards most of the hydrophilic solutes investigated. The derivatized sugars with the fluorescing 6-aminoquinoline tag were detected at a very low level of 7 × 10–8 mol/L, a fact that allowed the visualization of maltooligosaccharides up to a dp of 17.

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Abbreviations

c-AMP:

Adenosine-2’:3’-cyclic monophosphate

6-AQ:

6-Aminoquinoline

AIBN:

2,2’-Azobisisobutyronitrile

CPS:

Chloropropylsilyl-silica

CPTMS:

Chloropropyltrimethoxysilane

EDAC:

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

c-GMP:

Guanosine-2’:3’-cyclic monophosphate

p-HBA:

Para-Hydroxybenzoic acid

pNP:

Para-Nitrophenyl

c-UMP:

Uridine-2’:3’-cyclic monophosphate

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  1. Department of Chemistry, Oklahoma State University, Stillwater, OK, 74078-3071, USA

    Nilushi Paranamana & Ziad El Rassi

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  1. Nilushi Paranamana
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  2. Ziad El Rassi
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NP carried out the experimental studies, analysis, data interpretation, and wrote the manuscript. ZER supervised the entire work and edited the manuscript. Both the authors read and approved the final manuscript.

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Correspondence to Ziad El Rassi.

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Paranamana, N., El Rassi, Z. Precursor Carboxy-silica for Functionalization With Interactive Ligands. II. Carbodiimide Assisted Preparation of Silica Bonded Stationary Phases with D-glucamine for Hydrophilic Interaction Liquid Chromatography. Chromatographia 84, 781–791 (2021). https://doi.org/10.1007/s10337-021-04062-7

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