Production of Antitubercular Depsipeptides via Biosynthetic Engineering of Cinnamoyl Units

J Nat Prod. 2020 May 22;83(5):1666-1673. doi: 10.1021/acs.jnatprod.0c00194. Epub 2020 Apr 27.

Abstract

Two new cyclodecapeptides, atratumycins B (1) and C (2), containing substituted cinnamoyl side chains were generated by converging elements of the atratumycin (3) and atrovimycin (4) biosynthetic pathways. The structures of 1 and 2 were determined on the basis of HRESIMS, 1D and 2D NMR data, and X-ray single-crystal diffraction studies. Atratumycin B (1) is active against autoluminescent Mycobacterium tuberculosis H37Rv, displaying a minimum inhibitory concentration of 3.1 μg/mL (2.3 μM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology*
  • Biosynthetic Pathways
  • Crystallography, X-Ray
  • Depsipeptides / chemistry*
  • Depsipeptides / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mycobacterium tuberculosis / chemistry*
  • Mycobacterium tuberculosis / metabolism
  • Streptomyces / chemistry*

Substances

  • Antitubercular Agents
  • Depsipeptides
  • atratumycin