Structure Determination, Biosynthetic Origin, and Total Synthesis of Akazaoxime, an Enteromycin-Class Metabolite from a Marine-Derived Actinomycete of the Genus .

A new enteromycin-class antibiotic, akazaoxime (), possessing an aldoxime functionality in place of -methyl nitronic acid, was isolated from the cultured extract of a marine-derived actinomycete of the genus , along with known A-76356 (). The structure of , including the absolute stereochemistry of three chiral centers, was established by comprehensive analysis of nuclear magnetic resonance (NMR) and mass spectrometry data coupled with magnetic anisotropy analysis of its phenylglycine methyl ester derivatives. The stereochemistry of , not determined previously, was proven to be the same as that of on the basis of the similarity of their NMR and specific rotation data.