Utahmycins a and B, azaquinones produced by an environmental DNA clone

J Nat Prod. 2010 May 28;73(5):976-9. doi: 10.1021/np900786s.

Abstract

Two new azaquinones, utahmycins A (1) and B (2), were isolated from cultures of Streptomyces albus J1704 transformed with the environmental DNA-derived Erd gene cluster. The structures of 1 and 2 were elucidated by spectroscopic analyses. The structure of 1 was confirmed by single-crystal X-ray diffraction analysis. Both metabolites appear to arise from the addition of a nitrogen atom to erdacin biosynthetic intermediates. Utahmycin A (1) is the first example of a biologically derived 1,3-dimethyl-2-azaanthraquinone.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • DNA*
  • Molecular Conformation
  • Molecular Structure
  • Organisms, Genetically Modified
  • Quinones / chemistry
  • Quinones / isolation & purification*
  • Streptomyces / chemistry*
  • Streptomyces / genetics

Substances

  • Quinones
  • utahmycin A
  • utahmycin B
  • DNA