Oxidative rearrangement processes in the biosynthesis of Gilvocarcin V

Tao Liu, Carsten Fischer, Claus Beninga, Jürgen Rohr

Research output: Contribution to journalArticlepeer-review

45 Scopus citations


Gilvocarcin V (GV), an antitumor agent produced by Streptomyces griseoflavus Gö 3592 and various other streptomycetes, is the most important representative of the distinct family of benzo[d]naphtho[1,2-b]pyran-6-one aryl C-glycoside antibiotics, which show excellent antitumor activity and a remarkably low toxicity. The most intriguing step of its biosynthesis is an oxidative rearrangement cascade, in which the C-5/C-6 of an angucyclinone precursor bond is broken. Although this oxidative cleavage is essential for the formation of GV's unique chromophore and for GV's biological activity, and is likely to occur similarly in the biosyntheses of other angucyclinone-derived antibiotics, such as the kinamycins and the jadomycins, it is only poorly understood. Herein we report various experiments which shed light onto this intriguing oxidative cleavage reaction. These include incorporation studies with 18O-labeled precursors and the isolation and structure determination of novel intermediates of gilvocarcin biosynthesis accumulated by mutants, in which two genes encoding monooxygenases responsible for the C-C-bond cleavage of the gilvocarcin pathway, gilOI and gilOIV, were deleted through targeted PCR.

Original languageEnglish
Pages (from-to)12262-12263
Number of pages2
JournalJournal of the American Chemical Society
Issue number39
StatePublished - Oct 6 2004

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)
  • Biochemistry
  • Colloid and Surface Chemistry


Dive into the research topics of 'Oxidative rearrangement processes in the biosynthesis of Gilvocarcin V'. Together they form a unique fingerprint.

Cite this