Synthesis of paenipeptin C' analogues employing solution-phase CLipPA chemistry

Juliana T W Tong; Iman Kavianinia; Scott A Ferguson; Gregory M Cook; Paul W R Harris; Margaret A Brimble

doi:10.1039/d0ob00950d

Synthesis of paenipeptin C' analogues employing solution-phase CLipPA chemistry

Org Biomol Chem. 2020 May 29. doi: 10.1039/d0ob00950d. Online ahead of print.

Authors

Juliana T W Tong¹, Iman Kavianinia², Scott A Ferguson³, Gregory M Cook³, Paul W R Harris², Margaret A Brimble²

Affiliations

¹ School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland 1010, New Zealand. m.brimble@auckland.ac.nz and Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3 Symonds Street, Auckland, New Zealand.
² School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland 1010, New Zealand. m.brimble@auckland.ac.nz and School of Biological Sciences, The University of Auckland, 3A Symonds Street, Auckland 1010, New Zealand and Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3 Symonds Street, Auckland, New Zealand.
³ Department of Microbiology and Immunology, School of Medical Sciences, University of Otago, 720 Cumberland Street, Dunedin 9054, New Zealand.

PMID: 32469029
DOI: 10.1039/d0ob00950d

Abstract

We herein report the synthesis of analogues of the antimicrobial lipopeptide, paenipeptin C', by installing varying lipid moieties using thiol-ene CLipPA (Cysteine Lipidation on a Peptide or Amino Acid) chemistry. Biological evaluation against both Gram-negative and Gram-positive strains indicated that several analogues possessed potent broad-spectrum antimicrobial activity.