10046. Wildfire Toxin

Nomenclature

CAS number: 32190-57-1
N-[2-Amino-4-(3-hydroxy-2-oxo-3-azetidinyl)-1-oxobutyl]-l-threonine.
C11H19N3O6; mol wt 289.29.
C 45.67%, H 6.62%, N 14.53%, O 33.18%.

Description and references

Isoln from Pseudomonas tabaci, the bacterium responsible for wildfire disease of tobacco: Woolley et al., J. Biol. Chem. 197, 409 (1952). Highly toxic to a variety of organisms including bacteria, algae, higher plants and animals: Sinden et al., Toxicol. Appl. Pharmacol. 14, 82 (1969). Mode of action: Lovrekovich et al., Nature 197, 917; 198, 710 (1963). Structural studies: Woolley et al., J. Biol. Chem. 215, 485 (1955); Stewart, J. Am. Chem. Soc. 83, 435 (1961). Revised structure: idem, Nature 229, 174 (1971).

Chemical structure

Properties

Colorless, very hygroscopic substance. Very soluble in water; readily sol in methanol. Moderately sol in ethanol; sparingly sol in n-butanol and higher alcohols. Practically insol in acetone, ethyl acetate, and less polar organic liquids. Shows marked instability. Slowly loses potency in aq soln at pH 6. Complete loss of activity at these conditions and 0° in one month. Inactivation more rapid in methanol or when pH is shifted to either side of 6, esp in alkaline range.