2. Academic Validation
  3. Structures and biological activities of cycloheptamycins A and B

Structures and biological activities of cycloheptamycins A and B

  • Org Biomol Chem. 2019 Jul 21;17(27):6595-6600. doi: 10.1039/c9ob01261c.
Zhengyi Qian 1,  Janine Antosch 1,  Jutta Wiese 2,  Johannes F Imhoff 2,  Hans-Peter Fiedler 3,  Alexander Pöthig 4,  Tobias A M Gulder 5
Affiliations

Affiliations

  • 1 Biosystems Chemistry, Department of Chemistry and Center for Integrated Protein Sciences Munich, Technical University of Munich, Lichtenbergstraße 4, 85748 Garching, Germany.
  • 2 GEOMAR Helmholtz Center for Ocean Research Kiel, RD3 Marine Microbiology, Düsternbrooker Weg 20, 24105 Kiel, Germany.
  • 3 Institute of Microbiology, University of Tübingen, Auf der Morgenstelle 28, D-72076 Tübingen, Germany.
  • 4 Department of Chemistry and Catalysis Research Center (CRC), Technical University of Munich, Ernst-Otto-Fischer-Straße 1, 85748 Garching, Germany. alexander.poethig@tum.de.
  • 5 Biosystems Chemistry, Department of Chemistry and Center for Integrated Protein Sciences Munich, Technical University of Munich, Lichtenbergstraße 4, 85748 Garching, Germany and Chair of Technical Biochemistry, Technical University of Dresden, Bergstraße 66, 01069 Dresden, Germany. tobias.gulder@tu-dresden.de.
PMID: 31246217 DOI: 10.1039/c9ob01261c
Abstract

The heptadepsipeptide cycloheptamycin A was isolated from the terrestrial Streptomyces sp. Tü 6314. Its constitution was elucidated on the basis of NMR spectroscopic experiments and mass spectrometric analysis. Its stereostructure was investigated by peptide hydrolysis and derivatization and firmly established by X-ray structure analysis. In addition to the parent compound, a new cycloheptamycin analog, cycloheptamycin B, was discovered and structurally assigned using comparative MS/MS experiments and NMR. The biological profile of both compounds was investigated, revealing a selective inhibitory potential of cycloheptamycins against Propionibacterium acnes.

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