40957-90-2Relevant academic research and scientific papers
Studies on the Biosynthesis of Tabtoxin (Wildfire Toxin). Origin of the Carbonyl C-Atom of the β-Lactam Moiety from the C1-Pool
Mueller, Barbara,Haedener, Alfons,Tamm, Christoph
, p. 412 - 422 (2007/10/02)
Re-isolation of Pseudomonas tabaci strain NCPPB 2730 from its host, the tobacco plant, led to an activation of the bacteria in order to produce the β-lactam dipeptide tabtoxin (Wildfire toxin, 1).Incorporation of several 14C-labelled amino acids, as well as L-methionine, L-- and L-aspartate, rac-glycerol, and acetate into isotabtoxin (2) demonstrated that the building blocks of tabtoxin (1) are L-threonine, L-aspartate, the Me group of L-methionine and a C2-unit derived from the C3-pool.The Me gruop of L-methionine provides the carbonyl C-atom of the β-lactam moiety.These findings represent a novel pathway in β-lactam biosynthesis.Mechanistic aspects with respect to the β-lactam ring formation are discussed.A biradical 16 is proposed as an intermediate during the cyclization of a N-formyl-α-amino ketone 15.
Stereospecific synthesis of tabtoxin
Baldwin,Bailey,Gallacher,et al.
, p. 3695 - 3708 (2007/10/02)
Tabtoxin, the exotoxin from Pseudomonas tabaci (the organism responsible for Wildfire disease of tobacco plants), has been synthesized by a stereospecific route. The cycloaddition of an acylnitroso compound to a cyclohexadiene proceeded regioselectively t
Stereospecific Synthesis of Tabtoxin
Baldwin, Jack E.,Bailey, Patrick D.,Gallacher, Gerard,Singleton, Kevin A.,Wallace, Philip M.
, p. 1049 - 1050 (2007/10/02)
The exotoxin, Tabtoxin, from Pseudomonas tabaci (the organism responsible for Wildfire disease of tobacco plants) has been synthesised by a stereospecific route involving, as a key stereochemistry-defining step, the cycloaddition of an acylnitroso compoun
