Structure of Lipopolysaccharide Side-chain of Pseudomonas syringae pv. lachrymans Strain NCPPB 1096, in Relation to O-serogroup

Spitali, Mariangela; Smith, Andrew

doi:10.1046/j.1439-0434.2000.00576.x

Cited by 2 publications

(8 citation statements)

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“…(Spitali and Smith, 2000b: in the present study, rhamnose residues are given the same provisional labels, viz. A, B, C, for clarity):…”

Section: Resultsmentioning

confidence: 99%

“…were assigned to the anomeric carbons of β ‐GlcNAc(1→, 3,4)‐ α ‐Rha p (1→, 4)‐ α ‐Rha p (1→ and 3)‐ β ‐Rha p (1→, respectively, after consideration of the spectrum of side chain from P. syringae pv. lachrymans strain NCPPB 1096 (Spitali and Smith, 2000b). Signals at 173.4, 22.2, 61.9 and 56.1 p.p.m.…”

Section: Resultsmentioning

confidence: 99%

“…(Spitali and Smith, 2000b): in which d ‐ and l ‐rhamnose were present in equal proportion. Therefore, the periodate‐susceptible 1,4‐linked rhamnose was of the l ‐configuration, d ‐ and l ‐rhamnose being present in the intact side chain (I) in the ratio of 1 : 2.…”

Section: Resultsmentioning

confidence: 99%

“…(1985b). Periodate consumption during side chain oxidation was followed spectrophotometrically at 224 nm, and Smith degradations of intact side chain and derivative oligosaccharides were performed essentially according to Spitali and Smith (2000b) and Smith et al. (1985b; further details are given in ).…”

Section: Methodsmentioning

confidence: 99%

“…We have previously described the side chain structures of LPSs from strains of P. syringae pvs. morsprunorum , syringae (Spitali et al., 1995a), aptata , pisi and phaseolicola (Spitali et al., 1995b), tomato (Spitali and Smith, 2000a) and lachrymans (Spitali and Smith, 2000b), representative of the serogroups MOP1 and MOP2, APT‐PIS and PHA, TOM and LAC, respectively, in the typing system proposed by Samson and Saunier (1987). In this study, we report the side chain structure of strain NCPPB 79 (=CFBP 1615) of P. syringae pv.…”

Section: Introductionmentioning

confidence: 99%

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Structure of the Lipopolysaccharide Side Chain of Pseudomonas syringae pv. tabaci Strain NCPPB 79 (=CFBP 1615), in Relation to O‐serogroup

Spitali¹,

Smith²

2006

Journal of Phytopathology

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The lipopolysaccharide (LPS) side chain from Pseudomonas syringae pv. tabaci strain NCPPB 79 (¼CFBP 1615) contained l-and d-rhamnose, and GlcNAc. Using methylation analysis, periodate oxidation, Smith degradation and 1 H-and 13 C-nuclear magnetic resonance spectroscopy, the repeat unit was found to have the structure:This structure is correlated with a previously proposed serogrouping system. The involvement of LPS generally in plant disease is briefly discussed.

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“…(Spitali and Smith, 2000b: in the present study, rhamnose residues are given the same provisional labels, viz. A, B, C, for clarity):…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Structure of the Lipopolysaccharide Side Chain of Pseudomonas syringae pv. tabaci Strain NCPPB 79 (=CFBP 1615), in Relation to O‐serogroup

Spitali¹,

Smith²

2006

Journal of Phytopathology

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Synthesis of a β-(1→3)-d-Rhamnotetraose by a One-Pot, Multiple Radical Fragmentation

Crich¹,

Bowers²

2006

Org. Lett.

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A naturally-occurring β-(1→3)-D-rhamnotetraose has been constructed under conditions of sequential β -selective mannosylation controlled by the 4,6-O-[1-cyano-2-(2-iodophenyl)-ethylidene] protecting group. The route is concise, proceeding through a late stage radical deoxygenation that successfully uncovers all four deoxy subunits at once. E. hermanii is a member of the family of enterobacteriaceae, related to E. coli. It has been isolated from human wounds and sputum and has demonstrated pathogenicity against humans in vivo. 8 E. hermanii produces a β-lactamase and exhibits a distinctive antibiotic resistance, with resistance to penicillin, ampicillin, and carbenicillin. 9 Degradation studies have resulted in characterization of a repeat (1→3)-β-D-rhamnan from the cell walls of E. hermanii strain ATCC 33651. 10 The high content of the difficult β-D-rhamnosyl linkage, combined with its potential medicinal relevance make this LPS O-chain constituent an appropriate candidate for development of methods aimed at synthesis of the β-D-rhamnopyranosides.The stereoeoselective synthesis of the 1,2-cis-equatorial glycosidic bond as is found in both the β-mannosides and the β-rhamnosides is of perennial difficulty in carbohydrate chemistry. 11 Without the possibility of invoking neighboring group participation, the synthesis of such a linkage is rendered somewhat more sensitive than that of the trans-glycosidic bond. Captivated by this challenge, our group has found considerable success in employing the torsionally and electronically disarming 4,6-O-benzylidene protecting group. 12 In our researches this group has been used to synthesize a variety of β-D-mannopyranosides, including the (1→2), (1→4), and alternating (1→3), (1→4)-mannans. 13 However, even with this technology in hand, the challenge of the cis-glycosidic bond is considerably magnified in the biologically important rhamnopyranosides, which lack the functional arm for incorporation of a benzylidene-type directing effect.In general, strategies for synthesis of polysaccharides containing deoxy-sugars proceed via prior synthesis of an appropriately protected deoxy subunit, followed by extensive optimization of conditions for stereoselective glycosidation; recent efforts in this vein have been frustrated

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Structure of Lipopolysaccharide Side-chain of Pseudomonas syringae pv. lachrymans Strain NCPPB 1096, in Relation to O-serogroup

Abstract: The side-chain of lipopolysaccharide from the cucumber pathogen, Pseudomonas syringae pv. lachrymans strain NCPPB 1096, contained L-and D-rhamnose.

Cited by 2 publications

References 8 publications

Structure of the Lipopolysaccharide Side Chain of Pseudomonas syringae pv. tabaci Strain NCPPB 79 (=CFBP 1615), in Relation to O‐serogroup

Structure of the Lipopolysaccharide Side Chain of Pseudomonas syringae pv. tabaci Strain NCPPB 79 (=CFBP 1615), in Relation to O‐serogroup

Synthesis of a β-(1→3)-d-Rhamnotetraose by a One-Pot, Multiple Radical Fragmentation

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