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Keywords:

  • antibiotics;
  • biosynthesis;
  • cyclopentanone;
  • methylenomycin;
  • pentose;
  • Streptomyces
Thumbnail image of graphical abstract

How is the extraordinarily dense array of functional groups adorning the cyclopentane rings of the antibiotic methylenomycins assembled? Here it is shown that the northern 5 carbons of the methylenomycins (blue) derive from a pent(ul)ose intermediate of the pentose phosphate pathway. Together with previous results showing that the southern 4 carbons (green) derive from two acetate units and analysis of the mmy gene cluster that directs methylenomycin biosynthesis in Streptomyces coelicolor A3(2), these results suggest plausible early steps for methylenomycin biosynthesis via a butenolide intermediate.