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References to other databases: GTC:G24651SF, GlycomeDB:27347
Structural formula & atomic coordinates
Sweet-II 3D model
Show glycosyltransferases

This paper provides the first report of the molecular primary structure of the O-chain produced from A. radiobacter group M2-1. The repeating unit was determined, by means of chemical and spectroscopical analyses, to have the following structure: [3)-a-L-glycero-D-manno-heptose-(1-]n. The relevant feature of this structure is represented by the particular residue involved: L-glycero-D-manno-heptose. This monosaccharide is almost ubiquitous in Gram-negative bacteria, but it is exclusively located in the Core region and only in one other case has it is reported as an O-chain constituent. The knowledge of the chemical structure of the O-chain of A. radiobacter will be useful for comprehending the bacterium- host recognition mechanism at the molecular level.

L-glycero-D-manno-heptose, polysaccharide, O-chain, homopolymer, characterisation, Agrobacterium, Agrobacterium radiobacter

Publication DOI: 10.1002/ejoc.200400002
Journal NLM ID: 9805750
Publisher: Wiley-VCH
Correspondence: decastro@unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Universita` di Napoli, Complesso Universitario Monte Sante Angelo, Via Cintia 4, 80126 Napoli, Italy, Istituto di Chimica e Tecnologia dei Polimeri, CNR, Viale R. Margherita 6,95123 Catania, Italy
Methods: methylation, NMR-2D, NMR, Smith degradation, MALDI-TOF MS

This review reports and discusses the structural and the biological data available for the lipopolysaccharides from the Gram-negative bacterium Agrobacterium together with those of other related Rhizobiaceae species

Lipopolysaccharide, Rhizobium, symbiosis, Agrobacterium, Tumor induction

NCBI PubMed ID: 18353297
Publication DOI: 10.1016/j.carres.2008.01.036
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: decastro@unina.it; molinaro@unina.it
Institutions: Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Complesso Universitario Monte Sant' Angelo, Via Cinthia 4, 80126 Napoli, Italy
Methods: 13C NMR, 1H NMR, NMR-2D, MS, composition analysis, NMR-1D

The establishment of nitrogen-fixing symbiosis between a legume plant and its rhizobial symbiont requires that the bacterium adapt to changing conditions that occur with the host plant that both promotes and allows infection of the host root nodule cell, regulates and resists the host defense response, permits the exchange of metabolites, and contributes to the overall health of the host. This adaptive process involves changes to the bacterial cell surface and, therefore, structural modifications to the lipopolysaccharide (LPS). In this chapter, we describe the structures of the LPSs from symbiont members of the Rhizobiales, the genetics and mechanism of their biosynthesis, the modifications that occur during symbiosis, and their possible functions.

biosynthesis, lipopolysaccharides, structure, Rhizobium, symbiosis, plant defense

NCBI PubMed ID: 20593275
Publication DOI: 10.1007/978-90-481-9078-2_16
Publisher: Springer Science+Business Media B.V.
Correspondence: rcarlson@ccrc.uga.edu
Editors: Wang X, Quinn PJ
Institutions: Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Rd., Athens, GA 30602, USA

Bacteria from the Burkholderia cepacia complex (Bcc) cause highly contagious pneumonia among cystic fibrosis (CF) patients. Among them, Burkholderia cenocepacia is one of the most dangerous in the Bcc and is the most frequent cause of morbidity and mortality in CF patients. Indeed, it is responsible of 'cepacia syndrome', a deadly exacerbation of infection, that is the main cause of poor outcomes in lung transplantation. B. cenocepacia produces several soluble lectins with specificity for fucosylated and mannosylated glycoconjugates. These lectins are present on the bacterial cell surface and it has been proposed that they bind to lipopolysaccharide epitopes. In this work, we report on the interaction of one B. cenocepacia lectin, BC2L-A, with heptose and other manno configured sugar residues. Saturation Transfer Difference (STD) NMR spectroscopy studies of BC2L-A with different mono- and disaccharides demonstrated the requirement of manno configuration with hydroxyl or glycol group at C6 for the binding process. The crystal structure of BC2L-A complexed with the methyl-heptoside confirmed the location of the carbohydrate ring in the binding site and elucidated the orientation of the glycol tail, in agreement with NMR data. Titration calorimetry performed on monosaccharides, heptose disaccharides and bacterial heptose-containing oligosaccharides and polysaccharides confirmed that bacterial cell wall contains carbohydrate epitopes that can bind to BC2L-A. Additionally, the specific binding of fluorescent BC2L-A lectin on B. cenocepacia bacterial surface was demonstrated by electron microscopy.

Lipopolysaccharide, NMR, heptose, bacterial lectin, titration microcalorimetry

NCBI PubMed ID: 22763039
Publication DOI: 10.1093/glycob/cws105
Journal NLM ID: 9104124
Publisher: IRL Press at Oxford University Press
Correspondence: A.S. ; A.I.
Institutions: Dipartimento di Scienze Chimiche, Universita di Napoli 'Federico II', Napoli, Italy
Methods: 13C NMR, 1H NMR, X-ray, STD NMR, microcalorimetry, crystallization