The antibiotic responsible
for the high antiyeast and antifungal activity of a streptomycete fermentation
is shown to be the 9-methyl derivative (1) of streptimidone (2). The conjugated
diene system in (1) is assigned the 6E,8Z stereochemistry. Evidence is
presented for the biogenetic origin of the 9-methyl group in this streptimidone
homologue, and its antifungal activity is compared with that of streptimidone
and other fungicides.
Critical re-evaluation of
the published data, together with additional experimental evidence, establishes
that protomycin, previously suggested to have the structure (3), is identical
with the glutarimide antibiotic streptimidone (1).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.