Structures of carbohydrate units isolated from trout egg polysialoglycoproteins: Short-cored units with oligosialosyl groups

Nishimura, Hiroshi; Iwasaki, Mariko; Endo, Toshiya; Inoue, Sadako; Inoue, Yasuo; Matsumura, Go

doi:10.1016/0003-9861(82)90352-6

Cited by 89 publications

(31 citation statements)

References 9 publications

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“…The latter may be ascribed to steric hindrance of rotational freedom of I13Neu5Ac, as suggested in ref. 10. Otherwise, in addition to the disappearance of all doublings of signals in the anomeric ratio, and the replacement of Glc signals by Glc-01 signals, the H-l doublet of Gal-II was mainly influenced by the reduction, both as to chemical shift (for the alditol, 6 4.5%) as well as to the J1,* value (7.3 Hz).…”

Section: Resultsmentioning

confidence: 94%

A 500-MHz 1H-n.m.r. study of oligosaccharides derived from gangliosides by ozonolysis-alkaline fragmentation

Dorland

Halbeek

Vliegenthart

et al. 1986

Carbohydrate Research

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ABsTRAcrThe structural-reporter-group resonances in the 'H-n.m.r. spectra of a series of ganglioside-derived oligosaccharides are completely assigned. The three different types of sialic acid residues which may occur in these compounds could be adequately characterized. They are distinguishable on the basis of the set of ..chemical shifts of their H-3a and H-3e atoms. The mutual influence of GalNAc #I-(1+4) and NeuSAc (y-(2+3), both linked to the same Gal residue, on the 'H-n.m.r. parameters of each other, reflects a well-defined solution conformation, which is held to be responsible for the resistance of this "internal" sialic acid towards various sialidases. INTRODU(;TIONDuring the past decade, high-resolution lH-n.m.r. spectroscopy has become a powerful method in the structure determination of glycans derived from glycoproteins. Thanks to the availability of a consistent series of glycopeptides and oligosaccharides of gradually increasing structural complexity, we were able to develop empirical rules, correlating selective 'H-n.m.r. features with structural parameters: the "structural-reporter-group concept"1~2. When aiming to extend such 'H-n.m.r. studies to the field of glycolipid-ganglioside oligosaccharide chains, it should be *Dedicated to Roger W. Jeanloll. %esent address:

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Section: Resultsmentioning

confidence: 94%

A 500-MHz 1H-n.m.r. study of oligosaccharides derived from gangliosides by ozonolysis-alkaline fragmentation

Dorland

Halbeek

Vliegenthart

et al. 1986

Carbohydrate Research

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“…Free and bound sialic acid were quantified or monitored by the thiobarbituric acid method 132, 331 and the resorcinol method 1341, respectively. The molar ratios of component monosaccharides of oligosaccharides and glycoproteins were determined by GLC as previously reported [35]. The sulfate content was analyzed by HPLC on a TSK-gel IC-Anion PW column using a Jasco HPLC system equipped with 980-PU pump, a 970-UV detector, and a Rheodyne injector with a 20.~1 sample loop.…”

Section: Methodsmentioning

confidence: 99%

Occurrence and Structural Analysis of Highly Sulfated Multiantennary N‐linked Glycan Chains Derived from a Fertilization‐Associated Carbohydrate‐Rich Glycoprotein in Unfertilized Eggs of Tribolodon hakonensis

Taguchi

Iwasaki

Muto

et al. 1996

European Journal of Biochemistry

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This study represents the first detailed investigation of the nature of highly sulfated (keratan-sulfatelike) complex-type asparagine-linked glycans having a tetraantennary core structure and shows the effectiveness of fast-atom-bombardment mass spectrometric (FAB-MS) methods incorporating derivatization and mild methanolysis for analyzing such complex types of sulfated glycans.The structure of the N-glycan chains was unambiguously established by a combination of compositional analysis, methylation analysis, mild methanolysis for desulfation, hydrazinolysis/nitrous acid deamination, enzymatic (endo-P-galactosidase and peptide : N-gl ycosidase F) digestions, and instrumental analyses ('H-NMR spectroscopy and FAB-MS) which revealed the novel repeating sulfated carbohydrate sequences, 2 GalPl +4Gal,81[+4(HS03~6)GlcNAc~1-+3( -C GalPl--+4)Gal~l],-+ (see Structure I; p+q+r+s-14). This sequence is unique in: (a) the skeletal structure is similar to that of keratan sulfate but is completely devoid of 6-0-sulfated Gal residues and (b) the presence of branched Gal residues in the sequence -+4GlcNAc~1+3(Gal,81-4)GulPl+. +SO;b6+.Gav-l14 +SO,-b6 Abbreviations. FAB, fast atom bombardment; NeuSAc, N-acetylneuraminic acid; (2,5)-anhMan-ol, 2,5-anhydro-o-mannitol; Gal-ol, D-galactitol ; anhHex-ol, anhydro hexitol ; lD, one-dimensional ; 2D, two-dimensional.Enzymes. Endo-,8-galactosidase (EC 3.2.1.103); peptide:N-glycosidase F (EC 3.5.1.52). The oligosaccharide chains of keratan sulfate are bound to protein either by an N-glycosidic linkage (type I, as found in cornea) [21-241 or an 0-glycosidic linkage (type 11, associated with skin, cartilage, and bone) [25]. In the type I keratan sulfate derived from cornea, the core structures are restricted to diantennary [22-241. The existence of tri-or tetra-antennary complextype core structures carrying glycosaminoglycan chains has been reported in some mammalian cells [ I41 and virus-transformed baby hamster kidney cells [26], but these reports were mostly based on the results of Iectin-affinity chromatography using radioisotopes and the complete structures of these N-linked glycans have not yet been precisely determined.

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“…Carbohydrate Analyses-The monosaccharide compositions were determined by gas-liquid chromatography (GLC) as described previously (32). To determine the sialic acid content of WGA16, sialic acids were liberated directly by strong hydrolysis in 0.1 N TFA at 80°C for 2 h and then reacted with a volume of 1,2-diamino-4,5-methylenedioxybenzene reagent at 50°C for 2 h (33).…”

Section: Sds-page/lectin Blotting and Westernmentioning

confidence: 99%

Discovery, Primary, and Crystal Structures and Capacitation-related Properties of a Prostate-derived Heparin-binding Protein WGA16 from Boar Sperm

Garenáux

Kanagawa

Tsuchiyama

et al. 2015

Journal of Biological Chemistry

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Background: Mechanisms of glycoprotein redistribution during sperm capacitation remain unclear. Results: Prostate-specific ZG16-like lectin WGA16 was discovered in sperm lipid rafts. Its primary and crystal structure and GalT-and heparin-binding properties were characterized. Conclusion: Attachment to sperm via surface GalT and capacitation-induced detachment involve unique N-glycans and the heparin-binding domain. Significance: This is the first demonstration of a glycan-mediated mechanism for transient existence of seminal plasma glycoprotein on the sperm surface.

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Structures of carbohydrate units isolated from trout egg polysialoglycoproteins: Short-cored units with oligosialosyl groups

Cited by 89 publications

References 9 publications

A 500-MHz 1H-n.m.r. study of oligosaccharides derived from gangliosides by ozonolysis-alkaline fragmentation

A 500-MHz 1H-n.m.r. study of oligosaccharides derived from gangliosides by ozonolysis-alkaline fragmentation

Occurrence and Structural Analysis of Highly Sulfated Multiantennary N‐linked Glycan Chains Derived from a Fertilization‐Associated Carbohydrate‐Rich Glycoprotein in Unfertilized Eggs of Tribolodon hakonensis

Discovery, Primary, and Crystal Structures and Capacitation-related Properties of a Prostate-derived Heparin-binding Protein WGA16 from Boar Sperm

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