Production of Antitubercular Depsipeptides via Biosynthetic Engineering of Cinnamoyl Units
Zhijie Yang, Changli Sun, Zhiyong Liu, Qing Liu, Tianyu Zhang, Jianhua Ju, Junying Ma
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).
Topics & Concepts
DepsipeptideMycobacterium tuberculosisStereochemistryChemistryBiosynthesisSide chainTwo-dimensional nuclear magnetic resonance spectroscopyBiochemistryTuberculosisOrganic chemistryPolymerGeneMedicinePathologyMicrobial Natural Products and BiosynthesisBioactive Compounds and Antitumor AgentsCarbohydrate Chemistry and Synthesis