Platensimycin and platencin congeners from Streptomyces platensis.

Published

Journal Article

Platensimycin (1a) and platencin (2) are inhibitors of FabF and FabF/H bacterial fatty acid synthase. The discovery of natural congeners is an approach that can render a better understanding of the structure-function relationships of complex natural products. The isolation and structure elucidation of nine new congeners (11-20) of platensimycin and platencin are described from a fermentation broth of Streptomyces platensis. These hydroxylated congeners are likely derived by cytochrome P450 oxidation of the terpenoid units post-cyclization. Polar groups in the terpenoid portion of the molecule produce negative interactions with the hydrophobic pocket of FabF, resulting in poor activities. However, the discovery of these compounds serves an important purpose, not only to understand structure-function relationships, which cannot be easily accessed by chemical modification, but also to provide access to compounds that could be used for structural identification/confirmation of the oxidative trace metabolites produced in vivo during animal experiments.

Full Text

Duke Authors

Cited Authors

  • Zhang, C; Ondeyka, J; Herath, K; Jayasuriya, H; Guan, Z; Zink, DL; Dietrich, L; Burgess, B; Ha, SN; Wang, J; Singh, SB

Published Date

  • March 25, 2011

Published In

Volume / Issue

  • 74 / 3

Start / End Page

  • 329 - 340

PubMed ID

  • 21214253

Pubmed Central ID

  • 21214253

Electronic International Standard Serial Number (EISSN)

  • 1520-6025

Digital Object Identifier (DOI)

  • 10.1021/np100635f

Language

  • eng

Conference Location

  • United States