Poster Presentation 6th Modern Solid Phase Peptide Synthesis & Its Applications Symposium 2017

First total synthesis of PE2: A polypeptin with broad spectrum antibiotic activity (#50)

Simon J Mountford 1 , Biswaranjan Mohanty 1 , Kade D Roberts 1 2 , Heidi Y Yu 2 , Martin Scanlon 1 , Roger L Nation 2 , Tony Velkov 2 , Jian Li 2 , Philip Thompson 1
  1. Medicinal Chemsitry, Monash University, Parkville, VIC, Australia
  2. Drug Delivery, Disposition and Dynamics, Monash University, Parkville, VIC, Australia

The first total synthesis of a polypeptin, PE2, as well as the solution structure is reported. Synthesis in optically pure form confirms the proposed stereochemistry for the polypeptins at the 3-position on the 3-hydroxy depsipeptide moiety. We have also determined the NMR structure of PE2 in aqueous solution, showing it to form a stable ring conformation. The synthetic peptide shows anti-bacterial activity consistent with reports for naturally derived counterparts.