High-pressure liquid chromatography of neutral oligosaccharides: Effects of structural parameters

Blanken, Willem M.; Bergh, Michel L.E.; Koppen, Piet L.; Eijnden, Dirk H. van den

doi:10.1016/0003-2697(85)90369-0

Cited by 101 publications

(34 citation statements)

References 36 publications

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“…In addition, the GlcNAcp-containing oligosaccharide eluted before the Galp-containing oligosaccharide (cf. A4ciA4d) which is in further support of the HPLC rules as formulated by Blanken et al [26]. It is interesting to note that the GalNAca-containing oligosaccharide eluted before the GlcNAcp-containing oligosaccharide, irrespective of the nature of the sialic acid, cf.…”

Section: Discussionsupporting

confidence: 83%

Structure determination of five sialylated trisaccharides with core types 1, 3 or 5 isolated from bovine submaxillary mucin

Savage

Donoghue

D'Arcy

et al. 1990

European Journal of Biochemistry

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In this study we have investigated the structures of five sialylated trisaccharides released from bovine submaxillary mucin by alkaline borohydride treatment and isolated by high-performance liquid chromatography. Three of the trisaccharides contained NeuAc while two contained NeuGc. One oligosaccharide contained core-type 1, two contained core-type 3 and two contained core-type 5. The structures, determined by a combination of one-and two-dimensional 'H-NMR spectroscopy at 270 MHz and methylation analysis involving gas-liquid chromatography/mass spectrometry, were as follows : A4b, GalNAca(l4 3)[NeuAca(2 4 6)]CalNAcol; A4c,The oligosaccharides occurred in the approximate molar ratios 1 .O: 12.0: 0.3: 0.2: 2.0. This is the first report of oligosaccharides containing coretype 5 and of the occurrence of oligosaccharides A4b, A4e, and A4f in bovine submaxillary mucin. 'H-NMR data for structure A4e, which is a novel structure, are presented for the first time.Previous investigations of the smaller oligosaccharides released by alkaline borohydride treatment of bovine submaxillary mucin (BSM) [1, 21 have shown the presence of three acidic oligosaccharides : NeuAc(orNeuGc)a(2 + 6)GalNAcol, GalP(l+ 3)[NeuAca(2 + 6)]GalNAcol, and GlcNAcp(l+ 3)-[NeuAca(2 + 6)lGalNAcol. Differences in core types [3] have been reported in various submaxillary mucins. For instance, core-types 1 (GalP1 + 3GalNAc) and 3 (GlcNAcPl + 3Gal-NAc) have been found in bovine submaxillary mucin (BSM) [I, 2,4]; types 1 and 2 [GalPI --+ 3(GlcNAcPl --+ 6)GalNAcI in ovine submaxillary much [5 -71 while only core-type 1 has been found in porcine submaxillary mucin [S, 91. In this study we have extended the study of core types in BSM by determining the structures of oligosaccharides present in minor amounts. The structures were determined by analysis of the one-dimensional (1D) 'H-NMR spectra at 270 MHz in conjunction with the two-dimensional (2D) double quantum filtered (DQF) correlation spectroscopy (COSY) experiment. Methylation analysis results were in agreement with these structures. A preliminary account of this work has appeared [lo]. MATERIALS AND METHODSMucin was isolated from bovine submaxillary glands according to Tettamanti and Pigman [l 11, with modifications by Correspondence to A.

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Section: Discussionsupporting

confidence: 83%

Structure determination of five sialylated trisaccharides with core types 1, 3 or 5 isolated from bovine submaxillary mucin

Savage

Donoghue

D'Arcy

et al. 1990

European Journal of Biochemistry

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“…In some experiments, neutral ␤-eliminated oligosaccharides from PSGL-1 coexpressed with C2GnT and Fuc-TIV were treated with 0.25 milliunit/ml of ␣1-3/4-L-fucosidase in 20 l of 50 mM KH 2 PO 4 , pH 6.0, 0.1 M NaCl, 0.02% sodium azide at 37°C for 18 h. A portion of the oligosaccharides was analyzed by amine-adsorption high performance liquid chromatography on a Varian AX-5 column (4 mm ϫ 30 cm). The column was equilibrated in 65:35 (v/v) acetonitrile:deionized water and was eluted with a linear gradient of increasing water (0.33%/min) (29). Fractions (0.5 ml) were collected, and radioactivity in each fraction was determined by scintillation counting.…”

Section: Structural Analysis Of Psgl-1 Oligosaccharides-following Idementioning

confidence: 99%

Post-translational Modifications of Recombinant P-selectin Glycoprotein Ligand-1 Required for Binding to P- and E-selectin

Li¹,

Wilkins

Crawley

et al. 1996

Journal of Biological Chemistry

317

259

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P-selectin glycoprotein ligand-1 (PSGL-1) is a mucinlike ligand for P-and E-selectin on human leukocytes. PSGL-1 requires sialylated, fucosylated O-linked glycans and tyrosine sulfate to bind P-selectin. Less is known about the determinants that PSGL-1 requires to bind E-selectin. To further define the modifications required for PSGL-1 to bind P-and E-selectin, we transfected Chinese hamster ovary (CHO) cells with cDNAs for PSGL-1 and specific glycosyltransferases. CHO cells synthesize only core 1 O-linked glycans (Gal␤1-3Gal-NAc␣1-Ser/Thr); they lack core 2 O-linked glycans (Gal␤1-3(Gal␤1-4GlcNAc␤1-6)GalNAc␣1-Ser/Thr) because they do not express the core 2 ␤1-6-N-acetylglucosaminyltransferase (C2GnT). CHO cells also lack ␣1-3 fucosyltransferase activity. PSGL-1 expressed on transfected CHO cells bound P-and E-selectin only when it was co-expressed with both C2GnT and an ␣1-3 fucosyltransferase (Fuc-TIII, Fuc-TIV, or Fuc-TVII). Chromatography of ␤-eliminated O-linked glycans from PSGL-1 co-expressed with C2GnT confirmed synthesis of core 2 structures. Tyrosine residues on PSGL-1 expressed in CHO cells were shown to be sulfated. Phenylalanine replacement of three tyrosines within a consensus sequence for tyrosine sulfation abolished binding to Pselectin but not to E-selectin. These results demonstrate that PSGL-1 requires core 2 O-linked glycans that are sialylated and fucosylated to bind P-and E-selectin. PSGL-1 also requires tyrosine sulfate to bind P-selectin but not E-selectin.

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“…The advantages of the newly developed determination method are ease of operation and the use of an inexpensive instrument [1,2], Up to 40% can be reduced due to the simplicity of the operation, while up to50% can be reduced as a result of the economy of the machine [4,5]. References of statistical analysis were used.…”

Section: Resultsmentioning

confidence: 99%

Determination of Sugars in Sports Drinks

Fujita¹,

Tobino²

2012

J Nutr Food Sci

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Mono and disaccharides are routinely quantified with a differential refractometer. However, we developed a simpler analytical method involving pre-derivatization and high-performance liquid chromatography to achieve a high recovery rate. The purpose of our study was to understand the amount of sugar in sports drinks in order to determine marked consumption leads to tooth decay. Therefore, we quantified sugars in sports drinks.

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High-pressure liquid chromatography of neutral oligosaccharides: Effects of structural parameters

Cited by 101 publications

References 36 publications

Structure determination of five sialylated trisaccharides with core types 1, 3 or 5 isolated from bovine submaxillary mucin

Structure determination of five sialylated trisaccharides with core types 1, 3 or 5 isolated from bovine submaxillary mucin

Post-translational Modifications of Recombinant P-selectin Glycoprotein Ligand-1 Required for Binding to P- and E-selectin

Determination of Sugars in Sports Drinks

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