Rapid analysis of O-acetylated neuraminic acids by matrix assisted laser desorption/ionization time-of-flight mass spectrometry.

Abstract:

:N-Acetylneuraminic acid (a sialic acid) occurs mainly as a terminal substituent of oligosaccharides of glycoconjugates. Derivatives of neuraminic acid occur widely, substituted in the amino and hydroxy side chains, as well in the C-9 carbon skeleton. These derivatives are responsible for specific functions of sialic acids during cell-cell, cell-substrate, or cell-virus interactions. The study of O-acetylated neuraminic acids is difficult, because only small amounts are extractable from natural sources and they are generally unstable to acids and bases. We report a new method for the rapid analysis of O-acetylated neuraminic acids, using a combination of reversed phase HPLC and MALDI-TOF mass spectrometry. A mixture of neuraminic acids from bovine submaxillary gland mucins was analysed, as well as neuraminic acids variously substituted in the amino and hydroxy side chains with acetyl and glycolyl groups, respectively.

journal_name

Glycoconj J

journal_title

Glycoconjugate journal

authors

Stehling P,Gohlke M,Fitzner R,Reutter W

doi

10.1023/a:1006965600322

subject

Has Abstract

pub_date

1998-04-01 00:00:00

pages

339-44

issue

4

eissn

0282-0080

issn

1573-4986

journal_volume

15

pub_type

杂志文章
  • Glycosylation: a hallmark of cancer?

    abstract::The hallmarks of cancer are characterized by functional capabilities that allow cancer cells to survive, proliferate and disseminate during the multistep tumorigenesis. Cancer being a cellular disease, changes in cellular glycoproteins play an important role in malignant transformation and cancer progression. The pres...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章,评审

    doi:10.1007/s10719-016-9755-2

    authors: Vajaria BN,Patel PS

    更新日期:2017-04-01 00:00:00

  • Glycosylation in parasitic protozoa of the trypanosomatidae family.

    abstract::Over the last few years enormous interest has been shown in the structures of the glycan moieties of various parasite surface glycoconjugates. Structures have been determined for the glyco-components of glycosylphosphatidylinositol (GPI) protein membrane anchors, for asparagine-linked oligosaccharides, and for the gly...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章,评审

    doi:10.1007/BF00769843

    authors: Zamze S

    更新日期:1991-12-01 00:00:00

  • 6-O-sulfo sialylparagloboside and sialyl Lewis X neo-glycolipids containing lactamized neuraminic acid: synthesis and antigenic reactivity against G159 monoclonal antibody.

    abstract::Synthesis and antigenic reactivity of 6-O-sulfo sialylparagloboside (SPG) and sialyl Lewis X (sLeX) neo-glycolipids containing lactamized neuraminic acid are described. The suitably protected GlcNAc-beta (1-->3)-Gal-beta (1-->4)-GlcOSE derivative was glycosylated with NeuTFAc-alpha (2-->3)-Gal imidate to give NeuTFAc-...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/s10719-005-0352-z

    authors: Yamaguchi M,Ishida H,Kanamori A,Kannagi R,Kiso M

    更新日期:2005-03-01 00:00:00

  • Identification and characterization of the 4-epimerase AglW from the archaeon Methanococcus maripaludis.

    abstract::Archaea are ubiquitous single-cell microorganisms that have often adapted to harsh conditions and play important roles in biogeochemical cycles with potential applications in biotechnology. Methanococcus maripaludis, a methane-producing archaeon, is motile through multiple archaella on its cell surface. The major stru...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/s10719-018-9845-4

    authors: Sharma S,Ding Y,Jarrell KF,Brockhausen I

    更新日期:2018-12-01 00:00:00

  • Mass spectrometric analysis of genetic and post-translational heterogeneity in the lectins Jacalin and Maclura pomifera agglutinin.

    abstract::Jacalin and M. pomifera agglutinin are T-antigen specific lectins with alpha 4 beta 4 structures that show far greater micro-heterogeneity than plant lectins from other families, due to multiple genetic isoforms and post-translational processing. Electrospray mass spectrometry and combined liquid chromatography-electr...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/BF00731357

    authors: Young NM,Watson DC,Thibault P

    更新日期:1995-04-01 00:00:00

  • An expeditious synthesis of blood-group antigens, ABO histo-blood group type II antigens and xenoantigen oligosaccharides with amino type spacer-arms.

    abstract::Blood group oligosaccharides are one of the most clinically important antigen families and they may also act as secondary ligands for bacterial toxins from Escherichia coli and Vibrio cholerae. Herein we report the synthesis of spacered (sp = CH2CH2CH2NH2) glycosides of A antigen {α-D-GalNAc-(l→3)-[α-L-Fuc-(l→2)]-β-D-...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/s10719-015-9635-1

    authors: Karki G,Mishra VN,Mandal PK

    更新日期:2016-02-01 00:00:00

  • Site-specific characterization of N-linked glycosylation in human urinary glycoproteins and endogenous glycopeptides.

    abstract::Glycosylation is a very important post-translational modification involved in various cellular processes, such as cell adhesion, signal transduction and immune response. Urine is a rich source of glycoproteins and attractive biological fluid for biomarker discovery, owing to its availability, ease of collection, and c...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/s10719-016-9677-z

    authors: Kawahara R,Saad J,Angeli CB,Palmisano G

    更新日期:2016-12-01 00:00:00

  • Glycation of human lens proteins from diabetic and (nondiabetic) senile cataract patients.

    abstract::Glycation (nonenzymatic glycosylation) in the human lens (cortex and nucleus) in senile (nondiabetic) and diabetic cataracts was studied by measuring the extent of early and late glycation products, the content of free epsilon-amino groups and the formation of disulfide bonds in the soluble lens proteins. There was a ...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/BF00731255

    authors: Duhaiman AS

    更新日期:1995-10-01 00:00:00

  • Enzymic synthesis of the trisaccharide core region of the carbohydrate chain of N-glycoprotein.

    abstract::Transmannosylation from mannotriose (Man beta 1-4Man beta 1-4Man) to the 4-position at the nonreducing end N-acetylglucosaminyl residue of N,N'-diacetylchitobiose was regioselectively induced through the use of beta-D-mannanase from Aspergillus niger. The enzyme formed the trisaccharide Man beta 1-4GlcNAc beta 1-4GlcN...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/BF00731150

    authors: Usui T,Suzuki M,Sato T,Kawagishi H,Adachi K,Sano H

    更新日期:1994-04-01 00:00:00

  • Interactions of putative heparin-binding domains of basic fibroblast growth factor and its receptor, FGFR-1, with heparin using synthetic peptides.

    abstract::We have examined structure-function relationships that have been proposed to account for the heparin-binding properties of basic fibroblast growth factor and its receptor, FGFR-1, using synthetic peptides, DNA synthesis assays and binding assays in a resonant mirror biosensor. The results suggest that the interaction ...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1023/a:1006986104865

    authors: Kinsella L,Chen HL,Smith JA,Rudland PS,Fernig DG

    更新日期:1998-04-01 00:00:00

  • Unaltered complex N-glycan profiles in Nicotiana benthamiana despite drastic reduction of beta1,2- N -acetylglucosaminyltransferase I activity.

    abstract::UDP-GlcNAc:alpha3-D-mannoside beta1,2- N -acetylglucosaminyltransferase I (GnTI; EC 2.4.1.101) is a Golgi-resident glycosyltransferase that is essential for the processing of oligomannose to hybrid and complex N-glycans in higher eukaryotes. The cDNA of Nicotiana tabacum GnTI has been cloned and characterised previous...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1023/B:GLYC.0000045099.29038.04

    authors: Strasser R,Altmann F,Glössl J,Steinkellner H

    更新日期:2004-01-01 00:00:00

  • A novel acid polysaccharide from Boletus edulis: extraction, characteristics and antitumor activities in vitro.

    abstract::A novel cold-water-soluble polysaccharide (BEP), with a molecular weight of 6.0 × 106 Da, was isolated from Boletus edulis. BEP consists of galactose, glucose, xylose, mannose, glucuronic, and galacturonic acid in a ratio of 0.34:0.28:0.28:2.57:1.00:0.44. The IR results showed that BEP was an acid polysaccharide, cont...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/s10719-021-09972-0

    authors: Meng T,Yu SS,Ji HY,Xu XM,Liu AJ

    更新日期:2021-01-28 00:00:00

  • Three-dimensional structure of a glycosphingolipid having a novel carbohydrate linkage, Galbeta1-4(Fucalpha1-3)Glcbeta1-3Galbeta, determined by theoretical calculations.

    abstract::The novel glycosphingolipid, SEGLx (Galbeta1-4(Fucalpha1-3)Glcbeta1-3GalbetaCer), which was identified by us (Kawakami Y, et al. (1993) J Biochem 114: 677-83), shows a characteristic spectrum on 1H-NMR analysis, in which the anomeric proton resonances of a reducing end galactose and a glucose are split. To elucidate t...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1023/a:1006908020370

    authors: Kawakami J,Kawakami Y,Nakamura K,Kojima H,Ito S,Tamai Y

    更新日期:1998-02-01 00:00:00

  • Sulfated sialic acid-polymers inhibit the cytotoxic action of bee and snake venom.

    abstract::Colominic acid is an alpha2,8-linked sialic acid polymer produced by Escherichia coli. We found that synthetic sulfated-colominic acids (SC) remarkably inhibited the cytotoxicity of bee and snake venom toward mouse fibroblast cells, but colominic acids showed no inhibition themselves, indicating the important role of ...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1023/a:1007074410201

    authors: Oda Y,Kinoshita M,Hamada K,Nakayama K,Ohta Y,Yamaguchi S,Tsukada Y,Kawai Y,Kakehi K

    更新日期:1999-08-01 00:00:00

  • In vitro production of proteoglycans in the articular-epiphyseal cartilage of growing pigs.

    abstract::The failure of cartilage mineralization in osteochondrotic cartilage may be due to an impaired proteoglycan production. The in vitro production of proteoglycans was therefore studied in the joint cartilage of growing pigs, aged 9-18 weeks, after incubation of cartilage samples with 35S-sulfate. Cartilage was obtained ...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/BF00731147

    authors: Ekman S,Unger E,Kjellén L

    更新日期:1994-04-01 00:00:00

  • Glycosphingolipids in feces of germ-free rats as a source for studies of developmental changes of intestinal epithelial cell surface carbohydrates.

    abstract::Non-acid and acid glycosphingolipids were isolated from feces of one litter of germ-free rats from day 17 to day 51. Quantitative and qualitative changes described for small intestine of conventional rats [Bouhours D, Bouhours J-F (1981) Biochem Biophys Res Commun 99:1384-89] were also found in the feces of these germ...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/BF01047848

    authors: Larson G,Midtvedt T

    更新日期:1989-01-01 00:00:00

  • Structural characterization of blood group A glycosphingolipids recognized by the antibody 3G9-A.

    abstract::In this study, the antibody 3G9-A was assayed for activity against human erythrocyte glycosphingolipids. The antibody was found to recognize glycosphingolipid components from blood group A erythrocytes but not glycosphingolipids from blood group B or O erythrocytes. Subsequent investigation revealed that the glycosphi...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/BF00731482

    authors: Briggs JB,Mandrell R,Macher BA

    更新日期:1996-06-01 00:00:00

  • Haemophilus parainfluenzae has a limited core lipopolysaccharide repertoire with no phase variation.

    abstract::Cell surface lipopolysaccharide (LPS) is a well characterized virulence determinant for the human pathogen Haemophilus influenzae, so an investigation of LPS in the less pathogenic Haemophilus parainfluenzae could yield important insights. Using a panel of 18 commensal H. parainfluenzae isolates we demonstrate that th...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/s10719-012-9455-5

    authors: Young RE,Hood DW

    更新日期:2013-08-01 00:00:00

  • Specificity of human anti-carbohydrate IgG antibodies as probed with polyacrylamide-based glycoconjugates.

    abstract::The TF, Tn, and SiaTn glycotopes are frequently expressed in cancer-associated mucins. Antibodies to these glycotopes were found in human serum. A set of polyacrylamide (PAA)--based glycoconjugates was applied to the direct and competitive enzyme-linked immunosorbent assays (ELISA) to characterize the specificity of s...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1023/B:GLYC.0000018582.83813.04

    authors: Smorodin EP,Kurtenkov OA,Sergeyev BL,Pazynina GV,Bovin NV

    更新日期:2004-01-01 00:00:00

  • Evaluation of an amino acid residue critical for the specificity and activity of human Gb3/CD77 synthase.

    abstract::Human Gb3/CD77 synthase (α1,4-galactosyltransferase) is the only known glycosyltransferase that changes acceptor specificity because of a point mutation. The enzyme, encoded by A4GALT locus, is responsible for biosynthesis of Gal(α1-4)Gal moiety in Gb3 (CD77, Pk antigen) and P1 glycosphingolipids. We showed before tha...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/s10719-016-9716-9

    authors: Kaczmarek R,Mikolajewicz K,Szymczak K,Duk M,Majorczyk E,Krop-Watorek A,Buczkowska A,Czerwinski M

    更新日期:2016-12-01 00:00:00

  • 19F labelled glycosaminoglycan probes for solution NMR and non-linear (CARS) microscopy.

    abstract::Studying polysaccharide-protein interactions under physiological conditions by conventional techniques is challenging. Ideally, macromolecules could be followed by both in vitro spectroscopy experiments as well as in tissues using microscopy, to enable a proper comparison of results over these different scales but, of...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/s10719-016-9723-x

    authors: Lima MA,Cavalheiro RP,M Viana G,Meneghetti MCZ,Rudd TR,Skidmore MA,Powell AK,Yates EA

    更新日期:2017-06-01 00:00:00

  • Browning and pigmentation in food through the Maillard reaction.

    abstract::The Maillard reaction was discovered in 1912 by Louis C. Maillard when he observed the browning phenomena with aroma formation in a heated solution containing a sugar and an amino acid. The Maillard reaction starts from the reactions between carbonyl groups of various sugars and amino groups of amino acids/ proteins, ...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章,评审

    doi:10.1007/s10719-020-09943-x

    authors: Murata M

    更新日期:2020-09-10 00:00:00

  • Synthesis of Gal-beta-(1-->4)-GlcNac-beta-(1-->6)-[Gal-beta-(1-->3]-GalNAc-alpha- OBn oligosaccharides bearing O-methyl or O-sulfo groups at C-3 of the Gal residue: specific acceptors for Gal: 3-O-sulfotransferases.

    abstract::Our recent studies have revealed the existence of two distinct Gal: 3-O-sulfotransferases capable of acting on the C-3 position of galactose in a Core 2 branched structure, e.g., Galbeta1-->4GlcNAcbeta1-->6(Galbeta1-->3)GalNacalph a1-->OBenzyl as acceptor to give 3-O-sulfoGalbeta1-->4GlcNAcbeta1-->3(Galbeta1-->3)G alN...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1023/a:1006977607394

    authors: Jain RK,Piskorz CF,Chandrasekaran EV,Matta KL

    更新日期:1998-10-01 00:00:00

  • Quantitation of Glycopeptides by ESI/MS - size of the peptide part strongly affects the relative proportions and allows discovery of new glycan compositions of Ceruloplasmin.

    abstract::Significant changes of glycan structures are observed in humans if diseases like cancer, arthritis or inflammation are present. Thus, interest in biomarkers based on glycan structures has rapidly emerged in recent years and monitoring disease specific changes of glycosylation and their quantification is of great inter...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/s10719-018-9852-5

    authors: Baerenfaenger M,Moritz M,Meyer B

    更新日期:2019-02-01 00:00:00

  • Podocalyxin as a major pluripotent marker and novel keratan sulfate proteoglycan in human embryonic and induced pluripotent stem cells.

    abstract::Podocalyxin (PC) was first identified as a heavily sialylated transmembrane protein of glomerular podocytes. Recent studies suggest that PC is a remarkable glycoconjugate that acts as a universal glyco-carrier. The glycoforms of PC are responsible for multiple functions in normal tissue, human cancer cells, human embr...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章,评审

    doi:10.1007/s10719-016-9757-0

    authors: Toyoda H,Nagai Y,Kojima A,Kinoshita-Toyoda A

    更新日期:2017-04-01 00:00:00

  • A polysaccharide from Grifola frondosa relieves insulin resistance of HepG2 cell by Akt-GSK-3 pathway.

    abstract::Grifola frondosa is an important fungal research resource. However, there was little report about hyperglycemic activity of Grifola frondosa polysaccharide on insulin resistance in vitro. In this study, the hypoglycemic activity of a polysaccharide obtained from Grifola frondosa (GFP) on HepG2 cell and hpyerglycemic m...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/s10719-014-9526-x

    authors: Ma X,Zhou F,Chen Y,Zhang Y,Hou L,Cao X,Wang C

    更新日期:2014-07-01 00:00:00

  • Developmentally regulated O-acetylated sialoglycans in the central nervous system revealed by a new monoclonal antibody 493D4 recognizing a wide range of O-acetylated glycoconjugates.

    abstract::We have previously detected an alkali-labile and developmentally regulated antigen in rat embryonic cerebral cortex, which may be 9-O-acetylsialylated GT3 ganglioside (Hirabayashi Y, Hirota M, Suzuki Y, Matsumoto M, Obata K, Ando S (1989) Neurosci Lett 106:193-98). In this study we established a mouse monoclonal antib...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1023/a:1018542105832

    authors: Zhang G,Ji L,Kurono S,Fujita SC,Furuya S,Hirabayashi Y

    更新日期:1997-11-01 00:00:00

  • The preparation of a cold-water soluble polysaccharide from Grifola frondosa and its inhibitory effects on MKN-45 cells.

    abstract::In this study, a novel water soluble polysaccharide (named GFP-4) was extracted from Grifola frondosa at 4 oC, and its preliminary structure and inhibitory effects on human gastric carcinoma MKN-45 cells through the Fas/FasL death receptor apoptosis pathway were investigated. High-performance gel permeation chromatogr...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1007/s10719-020-09932-0

    authors: Liu C,Ji HY,Wu P,Yu J,Liu AJ

    更新日期:2020-08-01 00:00:00

  • Glycan microarrays of fluorescently-tagged natural glycans.

    abstract::This review discusses the challenges facing research in 'functional glycomics' and the novel technologies that are being developed to advance the field. The structural complexity of glycans and glycoconjugates makes studies of both their structures and recognition difficult. However, these intricate structures can be ...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章,评审

    doi:10.1007/s10719-015-9584-8

    authors: Song X,Heimburg-Molinaro J,Smith DF,Cummings RD

    更新日期:2015-10-01 00:00:00

  • Conformational analysis of methyl 6-O-[(R)- and (S)-1-carboxyethyl]-alpha-D-galactopyranoside by MM and Langevin dynamics simulations.

    abstract::The conformational space of methyl 6-O-[(R)- and (S)-1-carboxyethyl]-alpha-D-galactopyranoside has been investigated. A grid search employing energy minimization at each grid point over the three major degrees of freedom, namely phi, psi and omega, identified low energy regions. The R-isomer shows five low energy conf...

    journal_title:Glycoconjugate journal

    pub_type: 杂志文章

    doi:10.1023/a:1018527129939

    authors: Stenutz R,Widmalm G

    更新日期:1997-12-01 00:00:00