ABSTRACT
Prepiscibactin (1) is a possible intermediate in the biosynthesis of piscibactin, the siderophore responsible for the iron uptake of the bacterium Photobacterium damselae subsp. piscicida, the aethiological agent of fish pasteurellosis. Compound 1 was synthesized by a convergent approach starting from L-/D-cysteine and 2-hydroxybenzonitrile. The key steps were a highly diastereoselective SmI2-mediated Reformatsky reaction and Zn(2+)-induced asymmetric thiazolidine formation followed by lactamization. The absolute configuration 9R,10S,12R,13S was established for 1, and this confirmed the previous relative stereochemistry proposed on the basis of NOE and computational methods.
Subject(s)
Iodides/chemistry , Pfiesteria piscicida/chemistry , Photobacterium/chemistry , Samarium/chemistry , Thiazoles/chemistry , Thiazoles/chemical synthesis , Thiazolidines/chemistry , Zinc/chemistry , Animals , Cysteine/chemistry , Fish Diseases/microbiology , Fishes , Molecular Structure , Nitriles/chemistry , Pasteurella Infections/microbiology , Pasteurella Infections/pathology , StereoisomerismSubject(s)
Neurotoxicity Syndromes/diagnosis , Pfiesteria piscicida/pathogenicity , Protozoan Infections/diagnosis , Animals , Biological Factors/toxicity , Contrast Sensitivity , Environmental Exposure/adverse effects , Fish Diseases/microbiology , Fishes , Foodborne Diseases/microbiology , Health , Humans , Marine Toxins/toxicity , Neuropsychological Tests , Neurotoxicity Syndromes/epidemiology , Neurotoxicity Syndromes/microbiology , Pfiesteria piscicida/chemistry , Pfiesteria piscicida/isolation & purification , Protozoan Infections/microbiologyABSTRACT
Since its identification, the dinoflagellate Pfiesteria piscicida has been implicated in fish kills and fish disease in the southeastern United States. Adverse health effects have been reported in researchers working with the organism and in watermen following exposure to a fish kill in Maryland. A bioactive secretion is postulated as the cause of these effects but has not yet been isolated and chemically characterized. The biology and toxicology of this organism remain the topic of debate and research.
