Synthesis of tabtoxinine-.delta.-lactam

Lee, David L.; Rapoport, Henry

doi:10.1021/jo00912a005

Cited by 34 publications

(9 citation statements)

References 5 publications

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“…The biologically active β-lactam tabtoxin readily undergoes intramolecular transacylation on the stable but inactive δ-lactam isotabtoxin. The authors concluded that isotabtoxin appeared as an artifact of the workup, and no effort was made to isolate tabtoxin in its native form because the analysis of isotabtoxin was representative of the biosynthesis investigations [42]. This work established L-threonine as a direct precursor of the threonine moiety of tabtoxin.…”

Section: Chemical Structures Of Antimetabolite Toxinsmentioning

confidence: 99%

“…Thus, L-aspartic acid was established as the biogenetic origin of the side chain of tabtoxinine-β-lactam. The question of how β-lactam ring formation might proceed was subsequently raised [42]. A hypothetical mechanism for β-lactam ring closure in the biosynthesis of tabtoxin was formulated according to the mechanism of a similar photoprocess [43].…”

Section: Chemical Structures Of Antimetabolite Toxinsmentioning

confidence: 99%

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Chemical and Metabolic Aspects of Antimetabolite Toxins Produced by Pseudomonas syringae Pathovars

Arrebola

Cazorla

Pérez-Garcı́a

et al. 2011

Toxins

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Pseudomonas syringae is a phytopathogenic bacterium present in a wide variety of host plants where it causes diseases with economic impact. The symptoms produced by Pseudomonas syringae include chlorosis and necrosis of plant tissues, which are caused, in part, by antimetabolite toxins. This category of toxins, which includes tabtoxin, phaseolotoxin and mangotoxin, is produced by different pathovars of Pseudomonas syringae. These toxins are small peptidic molecules that target enzymes of amino acids’ biosynthetic pathways, inhibiting their activity and interfering in the general nitrogen metabolism. A general overview of the toxins’ chemistry, biosynthesis, activity, virulence and potential applications will be reviewed in this work.

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Section: Chemical Structures Of Antimetabolite Toxinsmentioning

confidence: 99%

Section: Chemical Structures Of Antimetabolite Toxinsmentioning

confidence: 99%

Chemical and Metabolic Aspects of Antimetabolite Toxins Produced by Pseudomonas syringae Pathovars

Arrebola

Cazorla

Pérez-Garcı́a

et al. 2011

Toxins

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“…Raaijmakers et al [39] described that TβL is proved to be difficult to synthesize due to the toxin’s instability. Tabtoxin is a relatively unstable molecule in vivo and during the procedures of toxin purification [40,41]. It has been demonstrated that the biological activity of a tabtoxin solution decreases with a half-life of approximately one day at room temperature [41].…”

Section: Discussionmentioning

confidence: 99%

Suppression of plant defense responses by extracellular metabolites from Pseudomonas syringae pv. tabaci in Nicotiana benthamiana

et al. 2013

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BackgroundPseudomonas syringae pv. tabaci (Pstab) is the causal agent of wildfire disease in tobacco plants. Several pathovars of Pseudomonas syringae produce a phytotoxic extracellular metabolite called coronatine (COR). COR has been shown to suppress plant defense responses. Interestingly, Pstab does not produce COR but still actively suppresses early plant defense responses. It is not clear if Pstab produces any extracellular metabolites that actively suppress early defense during bacterial pathogenesis.ResultsWe found that the Pstab extracellular metabolite extracts (Pstab extracts) remarkably suppressed stomatal closure and nonhost hypersensitive response (HR) cell death induced by a nonhost pathogen, P. syringae pv. tomato T1 (Pst T1), in Nicotiana benthamiana. We also found that the accumulation of nonhost pathogens, Pst T1 and P. syringae pv. glycinea (Psgly), was increased in N. benthamiana plants upon treatment with Pstab extracts . The HR cell death induced by Pathogen-Associated Molecular Pattern (INF1), gene-for-gene interaction (Pto/AvrPto and Cf-9/AvrCf-9) and ethanol was not delayed or suppressed by Pstab extracts. We performed metabolite profiling to investigate the extracellular metabolites from Pstab using UPLC-qTOF-MS and identified 49 extracellular metabolites from the Pstab supernatant culture. The results from gene expression profiling of PR-1, PR-2, PR-5, PDF1.2, ABA1, COI1, and HSR203J suggest that Pstab extracellular metabolites may interfere with SA-mediated defense pathways.ConclusionsIn this study, we found that Pstab extracts suppress plant defense responses such as stomatal closure and nonhost HR cell death induced by the nonhost bacterial pathogen Pst T1 in N. benthamiana.

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“…9 Thus, an effective synthetic procedure for the synthesis of TbL has been desired. In addition to synthetic studies 10 of (±)-1, 11a (-)-1, 11b its analogues, 12 2 13 and tabtoxinine-dlactam 4, 14 we have reported a short and efficient synthesis of (-)-1 and (3R)-1 as a preliminary communication. 15 Herein we describe details for the synthesis of the latter two compounds.…”

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confidence: 85%

Synthesis of (-)-Tabtoxinine-β-lactam, the Phytotoxin of Tobacco Wildfire Disease

Kiyota¹,

Takai²,

Shimasaki³

et al. 2007

Synthesis

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Synthesis of tabtoxinine-.delta.-lactam

Abstract: The mass spectrum exhibited significant peaks at m/e 424 (M+), 395 (M -CHO), 322 (M -CeHio02), 304 (M -C6H10O2 -H20), 293 (M -C6H10O2 -CHO), 85 (base peak, C5H9O), and 57 (C4H9).

Cited by 34 publications

References 5 publications

Chemical and Metabolic Aspects of Antimetabolite Toxins Produced by Pseudomonas syringae Pathovars

Chemical and Metabolic Aspects of Antimetabolite Toxins Produced by Pseudomonas syringae Pathovars

Suppression of plant defense responses by extracellular metabolites from Pseudomonas syringae pv. tabaci in Nicotiana benthamiana

Synthesis of (-)-Tabtoxinine-β-lactam, the Phytotoxin of Tobacco Wildfire Disease

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