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3′‐Enolpyruvyl‐UMP, a Novel and Unexpected Metabolite in Nikkomycin Biosynthesis

Nikkomycins are produced by several species of Streptomyces and exhibit fungicidal, insecticidal, and acaricidal properties due to their strong inhibition of chitin synthase. Structurally, they can be classified as peptidyl nucleosides containing two unusual amino acids, that is, hydroxypyridylhomothreonine and aminohexuronic acid with an N-glycosidically linked base (Scheme 1). Although the chemical structure of nikkomycins