Abstract
To examine the conformation-toxicity relationship concerning PM-toxins, which are the fungus (Phyllosticta maydis)-produced host-specific corn pathotoxins having C33- or C35-linear poly-β-ketol structures, five mimics were synthesized as stereoisomeric mixtures in addition to twelve that had previously been synthesized. The synthetic mimic PM-B', which has a 1, 3-diene spacer instead of the central saturated spacer in natural PM-toxin B, was 30- to 100-fold less toxic than the natural toxin, while PM-777B, C and D (which are isomers of PM-777A), and PM-77777 (which has six β-ketol groups) were as active as the natural toxin. These results suggest that the PMtoxins should take conformations (e.g., helix or hairpin forms) that are more involved than the previously considered simple ring-like forms.
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