Structural studies of the Vibrio cholerae O:3 O-antigen poly- saccharide

Chowdhury, Tofail A.; Jansson, Per‐Erik; Lindberg, Bengt; Lindberg, J. Johan; Gustafsson, Björn; Holme, Tord

doi:10.1016/0008-6215(91)84029-e

Cited by 36 publications

(14 citation statements)

References 14 publications

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“…O-Antigens from Vibrio cholerae strains may harbor Dglycero-D-manno-heptoses in both anomeric configurations. Thus, the O-antigenic polysaccharide from serogroup O:3 contains -heptosyl residues as constituent of a tetrasaccharide repeating unit [42], whereas serogroup O:21 contains a -linked D,D-heptosyl moiety [43]. In addition, -anomeric D-glycero-D-manno-heptosides and 6-deoxy-D-mannoheptosides (3) are present in the O-antigen from Plesiomonas shigelloides O54:H2 [44,45].…”

Section: Structural Variations and Occurrence Of Bacterial Heptoses Amentioning

confidence: 98%

Occurrence, Synthesis and Biosynthesis of Bacterial Heptoses

Kosma

2008

COC

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Heptoses are important higher-carbon sugars occurring in numerous structural variations in several domains of the bacterial cell wall, which are briefly summarized. Recent approaches towards the chemical and chemo-enzymatic synthesis of these microbial monosaccharides will be summarized as well as progress made in the elucidation of two major biochemical pathways involving the synthesis of heptose phosphates and nucleotide-activated heptoses.

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Section: Structural Variations and Occurrence Of Bacterial Heptoses Amentioning

confidence: 98%

Occurrence, Synthesis and Biosynthesis of Bacterial Heptoses

Kosma

2008

COC

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“…Bacillosamine has previously been found in the capsular polysaccharide from another marine bacteria, Pseudoalteromonas sp. KMM 155 [58] and in the O-antigens, among the others, of Pseudomonas aeruginosa [59], Pseudomonas aurantiaca IMB 31 [60], Pseudomonas reactans [61], Vibrio cholerae O3 [62], O5 [63], and O8 [64], Pseudoalteromonas haloplanktis KMM 223 [65], ATCC 14393 [66], KMM 634 [67,68]. Fuc4NAc has been found before in the cyclic enterobacterial common antigen from Yersinia pestis [69] and in the repeating unit of the O-chain polysaccharide of Pseudomonas fluorescens biovar A strain IMV 1152 [70] and of Pseudomonas sp.…”

Section: →3-α-d-galp-(1→6)-α-d-glcpnac-(1→4)-α-d-galpa-(1→3)-β-d-quipmentioning

confidence: 99%

Molecular Structure of Endotoxins from Gram-negative Marine Bacteria: An Update

Leone

2007

Mar. Drugs

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Marine bacteria are microrganisms that have adapted, through millions of years, to survival in environments often characterized by one or more extreme physical or chemical parameters, namely pressure, temperature and salinity. The main interest in the research on marine bacteria is due to their ability to produce several biologically active molecules, such as antibiotics, toxins and antitoxins, antitumor and antimicrobial agents. Nonetheless, lipopolysaccharides (LPSs), or their portions, from Gram-negative marine bacteria, have often shown low virulence, and represent potential candidates in the development of drugs to prevent septic shock. Besides, the molecular architecture of such molecules is related to the possibility of thriving in marine habitats, shielding the cell from the disrupting action of natural stress factors. Over the last few years, the depiction of a variety of structures of lipids A, core oligosaccharides and O-specific polysaccharides from LPSs of marine microrganisms has been given. In particular, here we will examine the most recently encountered structures for bacteria belonging to the genera Shewanella, Pseudoalteromonas and Alteromonas, of the γ-Proteobacteria phylum, and to the genera Flavobacterium, Cellulophaga, Arenibacter and Chryseobacterium, of the CytophagaFlavobacterium-Bacteroides phylum. Particular attention will be paid to the chemical features expressed by these structures (characteristic monosaccharides, non-glycidic appendages, phosphate groups), to the typifying traits of LPSs from marine bacteria and to

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“…The O-chain from the LPS of Helicobacter pylori strain D4 is a heptan polysaccharide having a trisaccharide repeating unit, [10] in which the only monosaccharide residue is a d-glycero-d-manno-heptose unit, as is also found in the complex O-chain polysaccharide from the bacterium Vibrio cholerae O:3. [11] Other examples are represented by two bac- www.eurjoc.org terial LPSs from Yersinia pseudotuberculosis serovar 1A [12] and Eubacterium saburreum, strain T27, [13] whose antigenic moieties are constituted by 6-deoxy-d-manno-heptose and d-glycero-d-galacto-heptose units, respectively.…”

Section: Resultsmentioning

confidence: 99%

Characterisation of the α‐(1→3) Homopolymer of L‐glycero‐D‐manno‐Heptose Units Isolated from the O‐Chain Polysaccharide of Agrobacterium radiobacter

Castro¹,

Sturiale²,

Parrilli³

2004

Eur J Org Chem

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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)‐α‐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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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Structural studies of the Vibrio cholerae O:3 O-antigen poly- saccharide

Cited by 36 publications

References 14 publications

Occurrence, Synthesis and Biosynthesis of Bacterial Heptoses

Occurrence, Synthesis and Biosynthesis of Bacterial Heptoses

Molecular Structure of Endotoxins from Gram-negative Marine Bacteria: An Update

Characterisation of the α‐(1→3) Homopolymer of L‐glycero‐D‐manno‐Heptose Units Isolated from the O‐Chain Polysaccharide of Agrobacterium radiobacter

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