Structure determination of tolaasin, an extracellular lipodepsipeptide produced by the mushroom pathogen, Pseudomonas tolaasii Paine

Journal of the American Chemical Society
1991.0

Abstract

The principal active component of tolaasin, the Pseudomonas tolaasii toxin, which is responsible for brown blotch disease of mushrooms, is shown to be a lipodepsipeptide of M, 1985. The structure determined is 8-hydroxyoctanoyl-ABut-~Pro-~Ser-D-Leu-~Val-D-Ser-~Leu-D-Val-~-Va~-D-Gln-~-Leu-D-Val-ABut-D-all~Thr-~-I~~~-H~-~Dab~-L~ (cyclized via lactone formation between D-affeThr and the C-terminus) by a combination of fast atom bombardment mass spectrometry (FABMS), 'H NMR, automated sequencing, and chiral gas chromatography. A minor component of the toxin (M, 1941) has a related structure in which the homoserine residue is substituted by glycine. In addition, the sequence of a modified form of the toxin, produced by a genetically engineered strain of P. tofaasii, is characterized.

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