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

Uiterweerd, M. T., Santiago, I. N., van der Heul, H., van Wezel, G. P. & Minnaard, A. J., 31-Aug-2020, In : European Journal of Organic Chemistry. 2020, 32, p. 5145-5152 8 p.

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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
Publication statusPublished - 31-Aug-2020

    Keywords

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

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