The biosynthesis of antibiotic F-244 in Fusarium sp. ATCC 20788: Origin of the carbon, hydrogen, and oxygen atoms

Endang Saefudin, P. Harrison

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6 Citations (Scopus)

Abstract

Biosynthetic incorporation experiments were performed with carbon-13 labelled precursors including sodium [1-13C]-, [2-13C], and [1,2-13C2]-acetate ar well as [methyl-13C] methionine into antibiotic F-244 (1) in growing cultures of Fusarium sp. ATCC 20788. After conversion to the methyl ester 2, analysis by NMR showed that the carbon skeleton of 1 derives from seven intact acetate units; the remaining four carbons are from methionine. Hence, the pathway is similar to that reported for 1 in Scopulariopsis. The biogenesis of the hydrogen atoms in 1 was also investigated. Incorporation of sodium [1-13C,18O2]acetate gives 2, which exhibits 18O-induced isotope shifts at C-1 and C-3. The labelling pattern is consistent with formation of the β-lactone ring by nucleophilic attack of a C-3 hydroxyl group in the nascent polyketide precursor onto the C-1 carbonyl.

Original languageEnglish
Pages (from-to)1-5
Number of pages5
JournalCanadian Journal of Chemistry
Volume73
Issue number1
DOIs
Publication statusPublished - 1 Jan 1995

Keywords

  • F-244
  • Fusarium
  • biosynthesis
  • polyketide
  • β-lactone

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