The metabolic pathways for the production of lincomycin, hormaomycin and the antitumor pyrrolo[1,4] benzodiazepines share an vinyl substituted pyrroline carboxylic acid (3-vinyl-2,3-pyrroline-5-carboxylic acid, VPCA) as a common intermediate. Biosynthesis of this vinyl substituted pyrroline carboxylic acid intermediate requires three enzymatic steps: two metalloenzymes and a C-C bond hydrolase. While the metabolic pathways to lincomycin, the PDBs and hormaomycin converge on VPCA , it has yet to be isolated and chemically characterized from <i>in vivo</i> or <i>in vitro</i> systems.  In order to isolate and characterize this putative biosynthetic intermediate, a coexpression system for the three enzymes was developed in order produce VPCA in culture. The biosynthesized small-molecules were purified from culture supernatants by solid-phase extraction and analyzed by ESI-MS and UV-Visible Spectroscopy.

Progress toward the chemical characterization 3-vinyl-2,3-pyrroline-5-carboxylic acid (VPCA): A bacterial, natural-product synthon

254th National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.