Analysis of Pyridylaminated O-Linked Sugar Chains by Two-Dimensional Sugar Mapping

Kuraya, Nahoki; Hase, Sumihiro

doi:10.1006/abio.1996.0029

Cited by 38 publications

(26 citation statements)

References 3 publications

(3 reference statements)

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“…The released glycans are thereafter derivatized at the reducing terminal with a fluorescent reagent and the derivatized glycan is subjected to a series of separation steps of which HILIC is often one. Derivatization reagents used are 2-aminopyridine [96,100,102,219], 2-aminobenzamide [220 -222], 2-aminoacridone [223,224], or 3-(acetylamino)-6-aminoacridine [225], and separations in HILIC mode have almost invariably taken place on various brands of amide silica [100, 102, 219, 221 -225]. These methods have been reviewed by Anumula [195,226].…”

Section: Glycansmentioning

confidence: 99%

“…Certain solutes seem to be more affected than others. [54,233,266]; pyridylaminated sialo sugar chains [219]; quaternary ammonium compounds [133]; small polar compounds in food analysis by HILIC/ESI-MS [155]; hydroxybenzoate saxitoxin analogs in dinoflagellates [160]; chitine fragments [198]; cyanobacterial toxins by HILIC/MS [164]; 1-deoxynojirimycin in mulberry leaves [150]; polar compounds contributing to umami taste and mouth-drying oral sensation of morel mushrooms [156]; elucidation of yeast sulfur metabolism [253]; PSP toxins [166,165,167]; monosaccharides [227,267]; identification of a bitter inhibitor [157] Peptides, nucleic acids, and other polar compounds [13]; peptides [67]; tyrosine protein-kinase specificity [234]; desalting of electroeluted proteins [241]; glycopeptides [268]; site-specific glycosylation microheterogeneity in recombinant human interferon-c [269]; urea, allantoin and lysine pyroglutamate in cosmetic samples [134]; glucosinolates in vegetables [201]; folates in human plasma by HILIC/ MS/MS [137]; citrulline in dried blood spots [138]; SPE enrichment of avoparcin from kidney samples [254]: Ionic compounds by pressurized flow CEC [270]; sucrose in a plasma-derived process solution [271]; glycoalkaloids in transgenic potatoes [104]; glycopeptide microheterogeneity [272] Peptides [67,68,276]; amphipathic a-helical peptides …”

Section: Underivatized Silicamentioning

confidence: 99%

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Hydrophilic interaction chromatography

Hemström

Irgum²

2006

J of Separation Science

1,074

818

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Separation of polar compounds on polar stationary phases with partly aqueous eluents is by no means a new separation mode in LC. The first HPLC applications were published more than 30 years ago, and were for a long time mostly confined to carbohydrate analysis. In the early 1990s new phases started to emerge, and the practice was given a name, hydrophilic interaction chromatography (HILIC). Although the use of this separation mode has been relatively limited, we have seen a sudden increase in popularity over the last few years, promoted by the need to analyze polar compounds in increasingly complex mixtures. Another reason for the increase in popularity is the widespread use of MS coupled to LC. The partly aqueous eluents high in ACN with a limited need of adding salt is almost ideal for ESI. The applications now encompass most categories of polar compounds, charged as well as uncharged, although HILIC is particularly well suited for solutes lacking charge where coulombic interactions cannot be used to mediate retention. The review attempts to summarize the ongoing discussion on the separation mechanism and gives an overview of the stationary phases used and the applications addressed with this separation mode in LC.

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Section: Glycansmentioning

confidence: 99%

Section: Underivatized Silicamentioning

confidence: 99%

Hydrophilic interaction chromatography

Hemström

Irgum²

2006

J of Separation Science

1,074

818

View full text Add to dashboard Cite

show abstract

“…They are powerful methods for the structural characterization of N-linked oligosaccharides, and consume only picomoles of samples. For example, a two-dimensional sugar mapping technique for pyridylaminated oligosaccharides [1][2][3] or a highperformance anion-exchange chromatography with a pulsed amperometric detector 4 are well known as high-resolution and sensitive methods.…”

mentioning

confidence: 99%

Separation of 2-Aminobenzoic Acid-Derivatized Glycosaminoglycans and Asparagine-linked Glycans by Capillary Electrophoresis

Sato

Ōkubo

et al. 2005

ANAL. SCI.

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Glycosylation is known to be the most common and diverse post-translational modification of proteins. It may affect their biological activity, solubility, stability, and immunogenicity. Therefore, determining the sugar structures has become increasingly important to understand and elucidate the functions of these molecules.To analyze carbohydrates, a high separation efficiency is required, because oligosaccharides have branched structures and comprise a variety of isomers and homologues. Chromatographic methods have recently been commonly used to identify the oligosaccharide structures in a glycoprotein. They are powerful methods for the structural characterization of N-linked oligosaccharides, and consume only picomoles of samples. For example, a two-dimensional sugar mapping technique for pyridylaminated oligosaccharides 1-3 or a highperformance anion-exchange chromatography with a pulsed amperometric detector 4 are well known as high-resolution and sensitive methods.High-performance capillary electrophoresis (HPCE), which is a relatively new separation technique, is known as a highresolution, simple and rapid method. Usually, it does not require any pretreatment steps, and permits analyses by a variety of separation modes simply by changing the selection of a running electrolyte solution. Thus, HPCE has extended its applicability to various kinds of carbohydrates, including monosaccharides, oligosaccharides, glycosaminoglycans (GAGs), and glycans of glycoproteins.5-10 These methods are superior in small sample consumption and easy operations to other methods including HPLC analyses.Because most of carbohydrates do not have strong absorbance in UV and visible regions, labeling procedures are necessary for HPCE analyses. 2-Aminobenzoic acid (2-AA) is a useful derivatizing reagent for carbohydrate analyses. [11][12][13][14][15][16][17][18] The 2-AA labeling procedure is rapid, selective, and easy to perform. 14 Moreover, 2-AA derivatives are able to become charged positively, negatively, or neutral, depending on the pH of a running buffer, since it has both a carboxyl group and an amino group. 15 This charge flexibility is suitable for multidimensional HPCE analysis. We have reported on a highly efficient derivatizing method and the determination of 2-AA-derivatized monosaccharides by HPCE with UV detection. 15,17,18 This method has advantages of simplicity, rapidness, high resolution, and high sensitivity. In the present paper, we report that the HPCE separations of 2-AA-derivatized GAGs and N-linked glycans of glycoproteins have also been achieved. Experimental ReagentsAll of the reagents were of the highest grade available and used without any further purification. Sodium cyanoborohydride was from Aldrich. Various sulfated heparinderived-∆-disaccharides and heparan sulfate-derived-∆-disaccharides, chondroitin sulfate-∆-disaccharides, hyaluronic acid, keratan sulfate from bovine cornea, glucose-oligomer, Nglycan, chondroitinase ABC, and keratenase II (Bacillus sp.) were all purchased from Seikagaku Kogyo Corp....

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“…For the carbohydrate analysis, various methods have been reported using GC, 1-3 LC 4-18 and CE, [19][20][21][22] and among them, HPLC with reductive amination 8,[10][11][12][13][14][15][16][17][18] is widely used. Reductive amination is a method which introduces chromophores or fluorophores onto the reducing end of the saccharides, and a number of reagents including 2-aminopyridine have been reported.…”

mentioning

confidence: 99%

Reversed-Phase HPLC of Monosaccharides in Glycoproteins Derivatized with Aminopyrazine with Fluorescence Detection

Hamase

Kiguchi

et al. 2000

ANAL. SCI.

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Determination of the components of monosaccharides and oligosaccharides in sugar chains is still an important technique for the biochemistry of glycoconjugates, and a sensitive, rapid and precise method is required. For the carbohydrate analysis, various methods have been reported using GC, 1-3 LC 4-18 and CE, [19][20][21][22] and among them, HPLC with reductive amination 8,[10][11][12][13][14][15][16][17][18] is widely used. Reductive amination is a method which introduces chromophores or fluorophores onto the reducing end of the saccharides, and a number of reagents including 2-aminopyridine have been reported. In the previous study, we investigated some aromatic amines, searching for a superior precolumn fluorescence derivatizing reagent for saccharides 23,24 and found that aminopyrazine is suitable for sensitive determination. In the study, 8 monosaccharides derivatized with aminopyrazine were completely separated by anion-exchange HPLC within 45 min. 24 The sensitivities for N-acetylated monosaccharides were about 4 times higher than those of neutral monosaccharides, suggesting that the selective determination could be carried out using aminopyrazine. However, the method has a disadvantage with respect to analytical time, and a rapid method is required. In addition, for the precise determination of components of monosaccharides in glycoconjugates, two-dimensional analysis is needed, and a method other than anion-exchange HPLC is required. Therefore, in this investigation, we describe a rapid reversed-phase HPLC method for the determination of monosaccharides derivatized with aminopyrazine; the determination of the components of monosaccharides in transferrin, fetuin and ovalbumin was carried out. The same samples were also determined by anion-exchange HPLC, and the values obtained by both methods were compared. In addition, to elucidate the chemical structures of the fluorophores and selectivity of aminopyrazine to the N-acetylated monosaccharide, we synthesized the glucose (Glc) derivative and Nacetylglucosamine (GlcNAc) derivative and investigated their fluorescence characteristics. Experimental MaterialsAminopyrazine and ribose were purchased from Nacalai Tesque (Kyoto, Japan).Dimethylamine-borane complex, acetonitrile of HPLC grade, Glc, galactose (Gal), mannose (Man), rhamnose (Rha), xylose (Xyl), fucose (Fuc), GlcNAc, Nacetylgalactosamine (GalNAc), and transferrin (human serum) were purchased from Wako Pure Chemical Industries (Osaka, Japan). Fetuin (bovine serum) was obtained from Sigma Chemical Co. (St. Louis, MO, USA); ovalbumin (chicken egg) was from Seikagaku Corporation (Tokyo, Japan). Silica gel 60 and Sephadex G-10 were obtained from Merck (Darmstadt, Germany) and Pharmacy Biotech (Uppsala, Sweden), respectively. Water was purified by the Milli-Q II system (Millipore, Bedford, MA, USA). Other reagents and solvents were of reagent grade. High performance liquid chromatographyThe HPLC system used was comprised of a Trirotar-V pump (Jasco, Tokyo, Japan), a 7125 injector (Rheodyne, Cotati, CA, USA...

show abstract

Analysis of Pyridylaminated O-Linked Sugar Chains by Two-Dimensional Sugar Mapping

Cited by 38 publications

References 3 publications

Hydrophilic interaction chromatography

Hydrophilic interaction chromatography

Separation of 2-Aminobenzoic Acid-Derivatized Glycosaminoglycans and Asparagine-linked Glycans by Capillary Electrophoresis

Reversed-Phase HPLC of Monosaccharides in Glycoproteins Derivatized with Aminopyrazine with Fluorescence Detection

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