Structural characterization of a novel acidic oligosaccharide unit derived from cow colostrum κ‐casein

Halbeek, Herman van; Dorland, L.; Vliegenthart, Johannes F.G.; Fiat, Anne‐Marie; Jollès, Pierre

doi:10.1016/0014-5793(81)80467-x

Cited by 57 publications

(19 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…That implies that these compounds have, in addition to NeuAc at C-6, a P-linked Gal residue attached to Structure 4. The NMR features of fractions 4 and 5a are identical; moreover, they are the same as those reported previously for the branched trisaccharide-alditol NeuAca-(2+6)[Galfl(1+3)]GalNA~-ol (compound A-4-2 in [15]; see also [14,16,17,211). The carbohydrate composition of the two fractions (Tdbk 2) is in keeping with this structure.…”

Section: Structure De Term In N T Ion Of' the Monosial-yl Oli~osacchusupporting

confidence: 82%

Isolation and structural characterization of low‐molecular‐mass monosialyl oligosaccharides derived from respiratory‐mucus glycoproteins of a patient suffering from bronchiectasis

Halbeek

Breg

Vliegenthart

et al. 1988

European Journal of Biochemistry

104

View full text Add to dashboard Cite

The carbohydrate chains of the respiratory-mucus glycoproteins of a patient suffering from bronchiectasis due to Kartagener's syndrome were released by alkaline borohydride treatment. Low-molecular-mass, monosialyl oligosaccharide-aldilols were isolated by anion-exchange chromatography and fractionated by consecutive straight-phase high-performance liquid chromatography (HPLC) on a silica-based alkylamine column, and reverse-phase HPLC on a silica-based octadecyl column, respectively. The structures of the oligosaccharidealditols were determined by 500-MHz H-NMR spectroscopy in combination with sugar composition analysis. The 24 structures established range in size from disaccharides to heptasaccharides. Novel oligosaccharides obtained from the bronchiectasis mucus glycoproteins are:23 of the 24 monosialyl oligosaccharides characterized can be conceived of as extensions of neutral oligosaccharides purified from the bronchial mucus of this patient

show abstract

Section: Structure De Term In N T Ion Of' the Monosial-yl Oli~osacchusupporting

confidence: 82%

Isolation and structural characterization of low‐molecular‐mass monosialyl oligosaccharides derived from respiratory‐mucus glycoproteins of a patient suffering from bronchiectasis

Halbeek

Breg

Vliegenthart

et al. 1988

European Journal of Biochemistry

104

View full text Add to dashboard Cite

show abstract

“…I H-5 (6 z 4.22 ppm). The deviation of this value from that observed so far in structures possessing the GlcNAc(P1+6)-GalNAc-ol element (6 z 4.28 ppm, compare compounds 2 -4 in Table 2) [8,9] is accounted for by the presence of the N-acetyllactosamine unit in (fll+6) linkage to Gal3 (see compound 14.5). Mutually, the chemical shift of H-I of Gal3 is slightly affected by introduction of GlcNAc6 ( A 6 z -0.01 ppm, as compared to compound 14.5).…”

Section: Some Oligosaccharid~-aldirols Obtainedfrom Porcine Blood-grmentioning

confidence: 58%

“…H-5 and H-6, as compared to the corresponding protons in fraction OS3 and alditol 1 [8,9]. The influences of introduction of the ix-linked GlcNAc residues upon the chemical shifts of the Gal3 and Gal4 reporter groups are independent of each other.…”

Section: ( P P~imentioning

confidence: 94%

“…So far, this technique was most successfully applied for the examination of the N-glycosidic types of glycoprotein oligosaccharide chains [l -61. Recently, it was employed also for the characterization of 0-glycosidic carbohydrate chains of the mucin type, like acidic oligosaccharide units from cow milk x-casein [7,8], neutral oligosaccharides from human bronchial mucin [9], and neutral and acidic carbohydrate chains from porcine submaxillary-mucin glycoproteins exhibiting blood-group A or H activity [7,10]. In this paper we report the 500-MHz 'H-NMR spectral parameters of the carbohydrate units of blood-group H substance from pig stomach cell linings.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Characterization of the Primary Structure and the Microheterogeneity of the Carbohydrate Chains of Porcine Blood-Group H Substance by 500-MHz 1H-NMR Spectroscopy

Halbeek¹,

Dorland²,

Vliegenthart³

et al. 1982

Eur J Biochem

107

View full text Add to dashboard Cite

In blood‐group H substance from pig stomach cell linings, carbohydrate structures are known to occur which are O‐glycosidically linked via GalNAc to Ser or Thr of the polypeptide backbone. They have in common the Gal(β1→3)GalNAc core unit, which bears one or more N‐acetyllactosamine branches. The latter are terminated either by Fuc in (α1→2) linkage or by GlcNAc in (α1→44) linkage to Gal. Both terminal sequences are considered to be porcine blood‐group H antigenic determinants. Employing 500‐MHz 1H‐NMR spectroscopy, the spectral features of the oligosaccharide‐alditols corresponding to these chains were established. Insight could be gained into the microheterogeneity displayed by some of the alditol fractions as to the distribution of the terminating Fuc and GlcNAc residues over the various branches. Such information can hardly be obtained using other approaches.

show abstract

“…The chemical shift of H-2 of GalNAc-ol(6 =4.387 ppm) indicates the presence of Gal in P(1+3)-linkage to GalNAc-ol [22]. The set of H-5 and H-6 chemical shifts of GalNAc-ol (6H-5 =4.265 ppm and 6H-6= 3.928 ppm) points to the presence of GlcNAc P(1+6)-linked to GalNAc-ol [21,22]. Based on the carbohydrate composition of fraction IV (Table 2), the occurrence of three H-1 doublets at 6 ~4 .…”

Section: Isolation and Characterization Of Oligosaccharide-ulditolsmentioning

confidence: 99%

Structural studies on the O-linked carbohydrate chains of human platelet glycocalicin

et al. 1984

View full text Add to dashboard Cite

Glycocalicin (140 kDa), constituting the main part of glycoprotein Ib (160 kDa), was released from the human platelet membrane by the action of a Ca2+-dependent protease, present in the platelet cytoplasm and liberated during sonication of the platelet suspension. After activation of the protease by Ca2+, the sonicated plateled suspension was subjected to differential centrifugation. The supernatant was applied to a column of wheat germ agglutinin linked to Sepharose 4B; glycocalicin was eluted from the column with 2.5 % (w/v) N-acetylglucosamine.carbohydrate by weight, representing N -as well as 0-glycosidically linked carbohydrate chains. The 0-glycosidic chains were split off by alkaline cleavage in the presence of 3H-labelled NaBH,. The liberated 3H-labelled oligosaccharide-alditols were fractionated on a DEAE-Sephadex A-25 column. The structures of the oligosaccharide-alditols were investigated by 500-MHz 'H-NMR spectroscopy. The major compound was identified as NeuAcu(2+3)GalP(l+ 3)[NeuAca(2+3)Gal~(l-t4)GlcNAc~(l-t6)]GalNAc-ol.Two minor compounds were found to be NeuAcu(2+3)GalP( 1 +3)[NeuAca(2+6)]GalNAc-ol and NeuAca(2-t 3)GalB(1+ 3)GalNAc-01. Glycocalicin was found to contain 40Platelet membrane glycoproteins play functional roles in vital processes such as platelet aggregation and adhesion 111. Glycoprotein Ib (160 kDa) is one of the main membrane glycoproteins. By the action of a Ca2 +-dependent protease, present in the platelet cytoplasm, glycocalicin (140 kDa), constituting the main part of glycoprotein Ib [2,3], can be cleaved from the platelet surface [4]. Glycoprotein Ib/glycocalicin is probably the receptor for Von Willebrand's factor in the presence of ristocetin [5] and for platelet adhesion to the vessel wall [6]. The carbohydrate chains of glycoprotein Ib may be involved in the aforementioned interaction phenomena.Glycocalicin was reported to have a carbohydrate content of 60 7; (w/w) comprising N-as well as 0-glycosidically linked carbohydrate chains [7 -91. The major 0-linked carbohydrate chain, isolated by Judson et al. [8], was shown to be a hexasaccharide-alditol containing N-acetylneuraminic acid, galactose, N-acetylglucosamine and N-acetylgalactosaminitol in the molar ratio 2 :2 : 1 : 1. Here we describe the elucidation, by 500-MHz 'H-NMR spectroscopy, of the primary structures of the prevalent 0-glycosidic carbohydrate chains of glycocalicin. A preliminary account of this study has been presented [lo]. During the preparation of the manuscript of this paper a report by Tsuji et al.[9] appeared describing the structure of the main 0-glycosidic chain, derived by methylation analysis in combination with enzymic degradation studies. MATERIALS AND METHODS Isolation of glycocalicin from human plateletsPlatelets (40 units were resuspended in 80 ml 10 mM Tris/HCl buffer, pH 8.0, containing 20 mM CaCI,. The suspension was cooled to 4 "C and sonicated for 2 min with a B-30 sonifier (Branson Sonic Power Company, Danbury, USA) (output control 7, 50% duty cycle; pulsed mode). After incubating the s...

show abstract

Structural characterization of a novel acidic oligosaccharide unit derived from cow colostrum κ‐casein

Cited by 57 publications

References 17 publications

Isolation and structural characterization of low‐molecular‐mass monosialyl oligosaccharides derived from respiratory‐mucus glycoproteins of a patient suffering from bronchiectasis

Isolation and structural characterization of low‐molecular‐mass monosialyl oligosaccharides derived from respiratory‐mucus glycoproteins of a patient suffering from bronchiectasis

Characterization of the Primary Structure and the Microheterogeneity of the Carbohydrate Chains of Porcine Blood-Group H Substance by 500-MHz 1H-NMR Spectroscopy

Structural studies on the O-linked carbohydrate chains of human platelet glycocalicin

Contact Info

Product

Resources

About