Sage Journals: Discover world-class research

Abstract

Saccharides (mono- to hexamers) that mimic the terminal epitopes of O-antigens of Vibrio cholerae O:1, serotypes Ogawa and Inaba have been studied by matrix-assisted laser desorption/ionization tandem time-of-flight (MALDI ToF/ToF) mass spectrometry (MS). Cationized adducts are the characteristic ions formed through the capture of sodium or potassium cations under MALDI MS conditions. Three characteristic pathways dominate in the fragmentation of model substances under MALDI ToF/ToF collision-induced dissociation MS/MS conditions of measurement. The first is the elimination which shortens the length of the oligosaccharide. In this way, conversion of the Ogawa to Inaba fragments takes place under the conditions of measurement. In the second, the conjugated transfer of electrons in the upstream unit of oligosaccharides takes place. The third route brings about the elimination of one α-hydroxy-γ-butyrolactone molecule from the 4-(3-deoxy-L-glycero-tetronamido) group. The MALDI ToF/ToF MS/MS provided sufficient information about molecular mass, the number of saccharide residues, the structure of saccharides, the C(4)- amide of 3-deoxy-L-glycero-tetronic acid (DGT) of the compounds investigated and allows Ogawa and Inaba serotypes to be distinguished.

Keywords

matrix assisted laser desorption/ionization time of flight/time of flight MALDI ToF/ToF positive tandem mass spectra

Get full access to this article

View all access options for this article.

References

Wang

Villeneuve

Zhang

Lei

Miller

Ch.E.

Lafaye

Nato

Szu

S.C.

Karpas

Bystrický

Robbins

J.B.

Kováč

Fournier

J.-M.

and Glaudemans

C.P.J.

, “On the antigenic determinants of the lipopolysaccharides of Vibrio cholerae O:1, serotypes Ogawa and Inaba”, J. Biol. Chem. 273, 2777 (1998). doi: 10.1074/jbc.273.5.2777

Kenne

Lindberg

Unger

Gustaffson

and Holme

, “Structural studies of the Vibrio cholera O-antigen”, Carbohydr. Res. 100, 341 (1982).

Hisatsune

Kondo

Isshiki

Iguchi

and Haishima

, “Occurrence of 2-O-methyl-N-(3-deoxy-l-glycero-tetronyl)-d-perosamine (4-amino-4,6-dideoxy-d-manno pyranose) in lipopolysaccharide from Ogawa but not from Inaba O-forms of O:1 Vibrio cholera”, Biochem. Biophys. Res. Commun. 190, 302 (1993). doi: 10.1006/bbrc.1993.1046

Ito

Higuchi

Hirobe

Hiramatsu

and Yokota

, “Identification of a novel sugar, 4-amino-4,6-dideoxy-2-O-methyl-mannose in the lipopolysaccharide of Vibrio cholerae O:1 serotype Ogawa”, Carbohydr. Res. 256, 113 (1994). doi: 10.1016/0008-6215(94)84231-0

Chernyak

Kondo

Wade

T.K.

Meeks

M.D.

Alzari

P.M.

Fournier

J.-M.

Taylor

R.K.

Kovác

and Wade

W.F.

, “Induction of protective immunity by synthetic Vibrio cholerae hexasacharide derived from V. Cholererae O:1 Ogawa lipopolysacharide bound to a protein carrier”, J. Infect. Dis. 185, 950 (2002). doi: 10.1086/339583

Saksena

Wade

T.K.

Kováč

and Wade

W. F.

, “Effect of saccharide length on the immunogenicity of neo-conjugates from synthetic fragments of the O-SP of Vibrio cholerae O1, serotype Ogawa”, Carbohydr. Res. 340, 2256 (2005). doi: 10.1016/j.carres.20 05.07.017

Saksena

Zhang

and Kováč

, “Immunogens from synthetic hexasaccharide fragment of the O-SP of Vibrio cholerae O:1, serotype Ogawa”, Tetrahedron: Asymetry 16, 187 (2005). doi: 10.1016/j.tetasy.2004.11.021

Kováčik

Pätoprstý

Oksmann

Mistrík

and Kováč

, “Electron ionization mass spectrometric study of monomeric models of O-polysaccharides of Vibrio cholerae O:1, serotypes Ogawa and Inaba”, J. Mass Spectrom. 38, 924 (2003). doi: 10.1002/jms.506

Kovácik

Bekešová

Tvaroška

and Kováč

, “Positive electrospray ion trap multistage mass spectrometric fragmentation of synthetic analogs of saccharide part of the lipopolysaccharides of Vibrio cholerae O:1”, J. Am. Soc. Mass Spectrom. 17, 749 (2006). doi: 10.1016/j.jasms.2006.02.006

10.

Bekešová

Kováčik

Chmelík

and Kováč

, “Negative electrospray, ion trap multistage mass spectrometry of synthetic fragments of the O-PS of Vibrio cholerae O:1”, Eur. J. Mass Spectrom., 12, 43 (2006). doi: 10.1255/ejms.790

11.

Lei

P. S.

Ogawa

and Kováč

, “Synthesis of the methyl α-glycosides of a di-, tri-, and a tetrasaccharide fragment mimicking the terminus of the O-polysaccharide of Vibrio Cholerae O:1, serotype Ogawa”, Carbohydr. Res. 281, 47 (1996). doi: 10.1016/0008-6215(95)00331-2

12.

Zhang

and Kováč

, “Synthesis of ligands related to the Vibrio Cholerae specific antigen. Part 14. Synthesis of methyl D-glycosides of some higher oligosacchairde fragments of Vibrio Cholerae O:1, serotype Inaba and Ogawa”, Carbohydr. Res. 300, 329 (2004).

13.

Gotoh

and Kováč

, “Synthesis of the methyl D-glycoside of the intracatenary disaccharide repeating unit of the O-polysaccharide of Vibrio Cholerae O:1. A comparison of two asembly strategies”, J. Carbohydr. Chem. 13, 1193 (1994).

14.

Lei

P.S.

Ogawa

and Kováč

, “Synthesis of the methyl D-glycoside of a trisaccharide mimicking the terminus of the O-antigen of Vibrio Cholerae O:1, serotype Inaba”, Carbohydr. Res. 279, 117 (1995). doi: 10.1016/0008-6215(95)00281-2

15.

Ogawa

Lei

P.S.

and Kováč

, “Synthesis of a functionalized hexasaccharide precursor of a glycoconjugate vaccine against cholera”, Bioorg. Med. Chem. Lett. 5(19), 2283 (1995). doi: 10.1016/0960-894X(95)00397-C

16.

Mistrík

, Mass Frontier 4.0; http://www.highchem.com/

17.

Domon

and Costello

C.E.A.

, “Systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates”, Glycoconj. J. 5, 397 (1988). doi: 10.1007/BF01049915

Positive-Ion Fragmentation in Matrix-Assisted Laser Desorption/Ionization Tandem Time-of-Flight Mass Spectrometry of Synthetic Analogs of the O-Specific Polysaccharide of Vibrio Cholerae O:1.

Abstract

Keywords

Get full access to this article

References