The first total synthesis and solution structure of a polypeptin, PE2, a cyclic lipopeptide with broad spectrum antibiotic activity. Issue 34 (16th August 2017)

• Record Type: Journal Article
• Authors: Mountford, Simon J.; Mohanty, Biswaranjan; Roberts, Kade D.; Yu, Heidi H.; Scanlon, Martin J.; Nation, Roger L.; Velkov, Tony; Li, Jian; Thompson, Philp E.
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 34(2017)
• Page Start: 7173
• Page End: 7180
• Publication Date: 2017-08-16
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob01493g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The synthesis and NMR structure of a polypeptin, a depsipeptide that shows anti-bacterial activity against drug resistant bacteria has been achieved. Abstract : The first total synthesis of a polypeptin, PE2, as well as its solution structure is reported. Synthesis in optically pure form confirms the proposed stereochemistry of 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.