Iso-maleimycin, a Constitutional Isomer of Maleimycin, fromStreptomycessp. QL37

Michiel T. Uiterweerd, Isabel Nunez Santiago, Helga van der Heul, Gilles P. van Wezel, Adriaan J. Minnaard*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

Iso-maleimycin, a previously unknown constitutional isomer of the antibiotic maleimycin, has been detected in an extract of Streptomyces sp. QL37. Chemical synthesis of both maleimycin (20 % yield over seven steps) and iso-maleimycin, (15 % yield over six steps) allowed access to reference materials for identification. Gas Chromatography coupled Mass Spectrometry (GC-MS) analysis demonstrated that of the two isomers, only iso-maleimycin was present in the extract. This finding supports our hypothesis that iso-maleimycin is a biosynthetic intermediate of lugdunomycin. Iso-maleimycin displays low antibiotic activity, with a Minimum Inhibitory Concentration (MIC) value on both E. coli and B. subtilis of 250 µg/mL.

Original languageEnglish
Pages (from-to)5145-5152
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number32
DOIs
Publication statusPublished - 31-Aug-2020

Keywords

  • Maleimycin
  • Streptomyces sp
  • Actinomycetes
  • Antibiotics
  • GC-MS
  • NATURAL-PRODUCTS
  • BIOSYNTHESIS
  • SHOWDOMYCIN
  • NITROSPOREUSINES
  • ANTIBIOTICS
  • ALKALOIDS

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