Structure of an acidic polysaccharide from a marine bacterium Pseudoalteromonas distincta KMM 638 containing 5-acetamido-3,5,7,9-tetradeoxy-7-formamido-l-glycero-l-manno-nonulosonic acid

Muldoon, Jimmy; Shashkov, Alexander S.; Senchenkova, Sof’ya N.; Tomshich, Svetlana V.; Komandrova, Nadezhda A.; Romanenko, Lyudmila A.; Knirel, Yuriy A.; Savage, Angela V.

doi:10.1016/s0008-6215(00)00280-9

Cited by 32 publications

(17 citation statements)

References 21 publications

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“…7A). These data are consistent with reported values in which the carbonyl carbon of a cis-formamido rotamer resonates 3-6 ppm upfield of the respective carbon of the transrotamer (39,(41)(42)(43).…”

Section: One-dimensional 1 H Nmr Spectroscopy Of the Formylated Produsupporting

confidence: 92%

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A Formyltransferase Required for Polymyxin Resistance in Escherichia coli and the Modification of Lipid A with 4-Amino-4-deoxy-l-arabinose

Breazeale

Ribeiro

McClerren

et al. 2005

Journal of Biological Chemistry

154

178

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Modification of the phosphate groups of lipid A with 4-amino-4-deoxy-L-arabinose (L-Ara4N Lipopolysaccharide (LPS)1 is an immunogenic glycolipid that constitutes most of the outer leaflet of the outer membrane of Gram-negative bacteria (1-4). LPS consists of three domains, which are the O-antigen, the core oligosaccharide, and the lipid A moiety (1-4). The O-antigen functions as a protective barrier, whereas the core sugars maintain outer membrane integrity and provide an attachment site for the O-antigen (1-4). Lipid A is the hydrophobic membrane anchor of LPS, and it is the active (endotoxin) component of LPS, accounting for many of the pathophysiological effects associated with Gram-negative sepsis (5-7).The Kdo 2 -lipid A portion of LPS is sufficient to support growth in Escherichia coli and Salmonella typhimurium (2). Covalent modifications to Kdo 2 -lipid A can be induced by environmental stimuli, such as low Mg 2ϩ concentrations or low pH (8 -10). As shown in Fig. 1 for S. typhimurium, these modifications include the incorporation of palmitate (11, 12), the addition of phosphoethanolamine (pEtN) (13-15), and/or the addition of 4-amino-4-deoxy-L-arabinose (L-Ara4N) moieties (13,16,17). The modification of at least one phosphate residue with L-Ara4N is required for maintaining resistance to certain cationic antimicrobial peptides of the innate immune system and to the antibiotic polymyxin (18,19). Resistance is due, in part, to the neutralization of the negative charges of lipid A by L-Ara4N, reducing the affinity of lipid A for cationic substances (20) and preventing these anti-microbial compounds from penetrating the outer membrane.The addition of pEtN and L-Ara4N groups to lipid A is controlled by the PmrA/PmrB two-component regulatory system, which is activated by low pH, high Fe 3ϩ levels, or indirectly, by low concentrations of Mg 2ϩ via the PhoP/PhoQ system through the action of PmrD (9). Activated PmrA stimulates transcription at the pmrCAB, pmrE(ugd) , and pmrHFIJKLM loci (19,21). Constitutive pmrA (pmrA c ) mutants of E. coli and S. typhimurium are polymyxin-resistant, and they modify their lipid A with L-Ara4N and pEtN groups under all growth conditions (17,18,22). Inactivation of either pmrE or the genes in the pmrHFIJKLM operon results in complete loss of polymyxin resistance and of L-Ara4N-modified lipid A in pmrA c bacterial cells (19,21,23). Similarly, pmrA c mutants harboring a nonpolar disruption of the pmrC(eptA) gene are unable * This research was supported by National Institutes of Health Grant GM-51310 (to C. R. H. R.). The Duke University NMR Center is partially supported by P30-CA-14236. NMR instrumentation in the Center was funded by the National Science Foundation, the National Institutes of Health, the North Carolina Biotechnology Center, and Duke University. The costs of publication of this article were defrayed in part by the payment of page charges. This article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fac...

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Section: One-dimensional 1 H Nmr Spectroscopy Of the Formylated Produsupporting

confidence: 92%

“…Certain Gram-negative bacteria possess LPS O-antigen sugars modified with formamido moieties (37,38,(41)(42)(43). Despite numerous examples of LPS sugars containing formamido groups, formamido-modified sugar nucleotides synthesized in vitro have not been reported previously.…”

Section: One-dimensional 1 H Nmr Spectroscopy Of the Formylated Produmentioning

confidence: 99%

A Formyltransferase Required for Polymyxin Resistance in Escherichia coli and the Modification of Lipid A with 4-Amino-4-deoxy-l-arabinose

Breazeale

Ribeiro

McClerren

et al. 2005

Journal of Biological Chemistry

154

178

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“…For example, l -iduronic acid [28], 2-acetamido-2-deoxyhexuronic acids with the d - galacto [29,30], l - galacto [29,31] and l - gulo [32] configurations, 3-deoxy- d - manno oct- 2-ulosonic acid [33,34], 5-acetamido-3,5,7,9-tetradeoxy-7-formamido- l - glycero - l - manno -non-2- ulosonic acid [30], 2,3-diacetamido-2,3-dideoxy- d -mannuronoyl- l -alanine [35], R -lactic acid [36], sulfate [37,38] and glycerophosphate [39] have been found among uncommon acidic components of the polysaccharides of Pseudoalteromonas .…”

Section: Structure Of Carbohydrate Antigens Of Gammaproteobacteriamentioning

confidence: 99%

The Structural Diversity of Carbohydrate Antigens of Selected Gram-Negative Marine Bacteria

2011

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Marine microorganisms have evolved for millions of years to survive in the environments characterized by one or more extreme physical or chemical parameters, e.g., high pressure, low temperature or high salinity. Marine bacteria have the ability to produce a range of biologically active molecules, such as antibiotics, toxins and antitoxins, antitumor and antimicrobial agents, and as a result, they have been a topic of research interest for many years. Among these biologically active molecules, the carbohydrate antigens, lipopolysaccharides (LPSs, O-antigens) found in cell walls of Gram-negative marine bacteria, show great potential as candidates in the development of drugs to prevent septic shock due to their low virulence. The structural diversity of LPSs is thought to be a reflection of the ability for these bacteria to adapt to an array of habitats, protecting the cell from being compromised by exposure to harsh environmental stress factors. Over the last few years, the variety of structures of core oligosaccharides and O-specific polysaccharides from LPSs of marine microrganisms has been discovered. In this review, we discuss the most recently encountered structures that have been identified from bacteria belonging to the genera Aeromonas, Alteromonas, Idiomarina, Microbulbifer, Pseudoalteromonas, Plesiomonas and Shewanella of the Gammaproteobacteria phylum; Sulfitobacter and Loktanella of the Alphaproteobactera phylum and to the genera Arenibacter, Cellulophaga, Chryseobacterium, Flavobacterium, Flexibacter of the Cytophaga-Flavobacterium-Bacteroides phylum. Particular attention is paid to the particular chemical features of the LPSs, such as the monosaccharide type, non-sugar substituents and phosphate groups, together with some of the typifying traits of LPSs obtained from marine bacteria. A possible correlation is then made between such features and the environmental adaptations undertaken by marine bacteria.

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“…An acidic polysaccharide isolated from Pseudoalteromonas distincta from a marine sponge contained two unusual acidic amino sugars, 2-acetamido-2-deoxy-Dgalaeturonic acid and 5-acetamido-3, 5, 7, 9-tetradeoxy-7-formamido-L-glycero-L-manno-nonulosonic acid (Muldoon and Shashkov, 2001). However, the bioactivities of these compounds were not reported.…”

Section: Bioactive Metabolites From Marine Organisms-associated Bacteriamentioning

confidence: 99%

Recent researches of bioactive metabolites in marine organisms-associated microorganisms

Jia

Cui

et al. 2004

J Ocean Univ. China

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Recent researches have shown that some compounds isolated from marine organisms have striking structural similarities with the metabolites from known microorganisms. It is inferred from the researches that the symbiotic or associated marine microorganisms may be the true sources of those compounds or at least involved in the biosynthesizing process. This view has been further evidenced by the researches for many sponges and sponge-associated microorganisms. Importantly, growing evidence has highlighted that the symbiotic or associated marine microorganisms live in the microenvironment within the hosts, and they also produce secondary metabolites which are new and original in structure and unique in activity. All these suggest that the microorganisms associated with marine organisms are the sources with very high potential to be new natural bioactive agents. This article reviews briefly the research advances in the study of new bioactive metabolites from marine organisms-associated microorganisms since 2000.

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Structure of an acidic polysaccharide from a marine bacterium Pseudoalteromonas distincta KMM 638 containing 5-acetamido-3,5,7,9-tetradeoxy-7-formamido-l-glycero-l-manno-nonulosonic acid

Cited by 32 publications

References 21 publications

A Formyltransferase Required for Polymyxin Resistance in Escherichia coli and the Modification of Lipid A with 4-Amino-4-deoxy-l-arabinose

A Formyltransferase Required for Polymyxin Resistance in Escherichia coli and the Modification of Lipid A with 4-Amino-4-deoxy-l-arabinose

The Structural Diversity of Carbohydrate Antigens of Selected Gram-Negative Marine Bacteria

Recent researches of bioactive metabolites in marine organisms-associated microorganisms

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