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Iso ‐maleimycin, a Constitutional Isomer of Maleimycin, from Streptomyces sp. QL37
Author(s) -
Uiterweerd Michiel T.,
Santiago Isabel Nuñez,
van der Heul Helga,
van Wezel Gilles P.,
Minnaard Adriaan J.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000767
Subject(s) - chemistry , streptomyces , yield (engineering) , mass spectrometry , stereochemistry , antibiotics , chromatography , bacteria , biochemistry , materials science , genetics , metallurgy , biology
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.