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
References
Garcia-Gomez D, Rodríguez-Gonzalo E, Carabias-Martınez R (2013) Stationary phases for separation of nucleosides and nucleotides by hydrophilic interaction liquid chromatography. TRAC-Trends Anal Chem 47:111–128
Gama MR, Silva RGC, Collins CH, Bottoli CBG (2012) Hydrophilic interaction chromatography. TRAC-Trends. Anal Chem 37:48–60
Guo Y (2015) Recent progress in the fundamental understanding of hydrophilic interaction chromatography (HILIC). Analyst 140:6452–6466
Euerby MR, Hulse J, Petersson P, Vazhentsev A, Kassam K (2015) Retention modelling in hydrophilic interaction chromatography. Anal Bioanal Chem 407:9135–9152
Fu Q, Liang T, Zhang X, Du Y, Guo Z, Liang X (2010) Carbohydrate separation by hydrophilic interaction liquid chromatography on a ‘click’ maltose column. Carbohydr Res 345:2690–2697
Greco G, Letzel T (2013) Main interactions and influences of the chromatographic parameters in HILIC separations. J Chromatogr Sci 51:684–693
Dinh NP, Jonsson T, Irgum K (2011) Probing the interaction mode in hydrophilic interaction chromatography. J Chromatogr A 1218:5880–5891
Yoshida T (2004) Peptide separation by hydrophilic interaction chromatography: a review. J Biochem Bioph Meth 60:265–280
Berthod A, Chang SS, Kullman JP, Armstrong DW (1998) Practice and mechanism of HPLC oligosaccharide separation with a cyclodextrin bonded phase. Talanta 47:1001–1012
Buszewski B, Noga S (2012) Hydrophilic interaction liquid chromatography (HILIC)—a powerful separation technique. Anal Bioanal Chem 402:231–247
Rathnasekara R, El Rassi Z (2017) Polar silica-based stationary phases. Part I - Singly and doubly layered sorbents consisting of TRIS-silica and chondroitin sulfate A-TRIS-silica for hydrophilic interaction liquid chromatography. Electrophoresis 38:1582–1591
Pereira AS, Giro´n AJ, Admasu E, Sandra P (2010) Green hydrophilic interaction chromatography using ethanol–water–carbon dioxide mixtures. J Sep Sci 33:834–837
Olsen BA (2001) Hydrophilic interaction chromatography using amino ad silica columns for the determination of polar pharmaceuticals and impurities. J Chromatogr A 913:113–122
Guo Y, Gaiki S (2011) Retention and selectivity of stationary phases for hydrophilic interaction chromatography. J Chromatogr A 1218:5920–5938
Jandera P (2011) Stationary and mobile phases in hydrophilic interaction chromatography: a review. Anal Chim Acta 692:1–25
Rathnasekara R, Khadka S, Jonnada M, El Rassi Z (2017) Polar and nonpolar organic polymer-based monolithic columns for capillary electrochromatography and high-performance liquid chromatography. Electrophoresis 38:60–79
Gunasena DN, El Rassi Z (2012) Organic monoliths for hydrophilic interaction electrochromatography/chromatography and immunoaffinity chromatography. Electrophoresis 33:251–261
Armstrong DW, ** HL (1989) Evaluation of the liquid chromatographic separation of monosaccharides, disaccharides, trisaccharides, tetrasaccharides, deoxysaccharides and sugar alcohols with stable cyclodextrin bonded phase columns. J Chromatogr A 462:219–232
Schuster G, Lindner W (2011) Chocolate HILIC phases: development and characterization of novel saccharide-based stationary phases by applying non-enzymatic browning (Maillard reaction) on amino-modified silica surfaces. Anal Bioanal Chem 400:2539–2554
Bicker W, Wu J, Lämmerhofer M, Lindner W (2008) Hydrophilic interaction chromatography in nonaqueous elution mode for separation of hydrophilic analytes on silica-based packings with noncharged polar bondings. J Sep Sci 31:2971–2987
Kawachi Y, Ikegami T, Takubo H, Ikegami Y, Miyamoto M, Tanaka N (2011) Chromatographic characterization of hydrophilic interaction liquid chromatography stationary phases: hydrophilicity, charge effects, structural selectivity, and separation efficiency. J Chromatogr A 1218:5903–5919
Alharthi S, El Rassi Z (2018) Poly(2-carboxyethyl acrylate-co-ethylene glycol dimethacrylate) monolithic precursor. Part II. Carbodiimide assisted post-polymerization modification with tris and d-Glucamine for use in hydrophilic interaction capillary liquid chromatography. J Liq Chrom & Relat Technol 41:684–691
Peng X, Liu T, Ji S, Feng Y (2013) Preparation of a novel carboxyl stationary phase by “thiol-ene” click chemistry for hydrophilic interaction chromatography. J Sep Sci 36:2571–2577
Paranamana N, El Rassi Z (2020) Precursor carboxy-silica for functionalization with interactive ligands. I. Carbodiimide-assisted preparation of silica-bonded stationary phases with octadecyl, naphthyl, and anthracenyl ligands: comparison of their selectivity and retentivity. J Sep Sci 43:4424–4433
Nashabeh W, El Rassi Z (1992) Capillary zone electrophoresis of linear and branched oligosaccharides. J Chromatogr A 600:279–287
Zhuravlev LT, Potapov VV (2006) Density of silanol groups on the surface of silica precipitated from a hydrothermal solution. Russ J Phys Chem 80:119–1128
Colin H, Guiochon G, Yun Z, Diez-Masa JC, Jandera J (1983) Selectivity for homologous series in reversed-phase LC: investigation of non-specific selectivity. J Chromatogr Sci 21:179–184
Smith JT, Nashabeh W, El Rassi Z (1994) Micellar electrokinetic capillary chromatography with in situ charged micelles.1. Evaluation of N-D-gluco-N-methylalkanamide surfactants as anionic borate complexes. Anal Chem 66:1119–1133
Brynes PJ, Bevilacqua P, Green A (1981) 6-aminoquinoline as a fluorogenic leaving group in peptide cleavage reactions: a new fluorogenic substrate for chymotrypsin. Anal Biochem 116:408–413
Mallik AK, Guragain S, Rahman MM, Takafuji M, Ihara H (2019) L-Lysine-derived highly selective stationary phases for hydrophilic interaction chromatography: effect of chain length on selectivity, efficiency, resolution, and asymmetry. Sep Sci Plus 2:42–50
Tyteca E, Guillarme D, Desmet G (2014) Use of individual retention modeling for gradient optimization in hydrophilic interaction chromatography: separation of nucleobases and nucleosides. J Chromatogr A 1368:125–131
Rathnasekara R, El Rassi Z (2017) Polar silica-based stationary phases. Part II- Neutral silica stationary phases with surface bound maltose and sorbitol for hydrophilic interaction liquid chromatography. J Chromatogr A 1508:24–32
Svec F, Fréchet J (1992) Continuous rods of macroporous polymer as high performance liquid chromatography separation media. Anal Chem 64:820–822
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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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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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DOI: https://doi.org/10.1007/s10337-021-04062-7