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Glycobiology Advance Access originally published online on January 3, 2008
Glycobiology 2008 18(3):260-269; doi:10.1093/glycob/cwm140
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© The Author 2008. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oxfordjournals.org

Full structural characterization of Shigella flexneri M90T serotype 5 wild-type R-LPS and its {Delta}galU mutant: glycine residue location in the inner core of the lipopolysaccharide

Antonio Molinaro1,2, Alba Silipo2, Cristina De Castro2, Luisa Sturiale3, Giulia Nigro4, Domenico Garozzo3, Maria Lina Bernardini4,5,, Rosa Lanzetta2 and Michelangelo Parrilli2

2 Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli Federico II, Via Cintia 4, I-80126 Napoli
3 CNR Istituto per la Chimica e la Tecnologia dei Materiali Polimerici, Viale A. Doria 6, 95125 Catania
4 Dipartimento di Biologia Cellulare e dello Sviluppo, Sapienza-Università di Roma, Via dei Sardi 70, 00185 Roma
5 Istituto Pasteur-Fondazione Cenci Bolognetti, Sapienza-Università di Roma, Piazzale Aldo Moro 5, 00185 Roma, Italy

1 To whom correspondence should be addressed: Fax: +39-081-674393; e-mail: molinaro{at}unina.it

Received on December 4, 2007; revised on December 28, 2007; accepted on December 29, 2007

Shigella flexneri is a Gram-negative bacterium responsible for serious enteric infections that occur mainly in the terminal ileum and colon. High interest in Shigella, as a human pathogen, is driven by its antibiotic resistance and the necessity to develop a vaccine against its infections. Vaccines of the last generation use carbohydrate moieties of the lipopolysaccharide as probable candidates. For this reason, the primary structure of the core oligosaccharide from the R-LPS produced by S. flexneri M90T serotype 5 using chemical analysis, nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MALDI), is herein reported. This is the first time that the core oligosaccharide primary structure by S. flexneri M90T is established in an unambiguous multidisciplinary approach. Chemical and spectroscopical investigation of the de-acetylated LPS showed that the inner core structure is characterized by a L,D-Hep-(1 ->7)-L,D-Hep-(1 ->3)-L,D-Hep-(1 ->5)-[Kdo-(2 ->4)]-Kdo sequence that is the common structural theme identified in Enterobacteriaceae. In particular, in S. flexneri M90T serotype 5 LPS, a glucosamine residue is additionally sitting at O-7 of the last heptose whereas the outer core is characterized by glucose and galactose residues. Also, in order to exactly define the position of glycine that is an integral constituent of the core region of the LPS, we created a S. flexneri M90T {Delta}galU mutant and studied its LOS. In this way it was possible to establish that glycine is sitting at O-6 of the second heptose in the inner core.

Key words: Glycine / lipooligosaccharide / mass spectrometry / NMR spectroscopy / Shigella flexneri


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