Issue 23, 2020
From the journal:

Organic & Biomolecular Chemistry

Synthesis of paenipeptin C′ analogues employing solution-phase CLipPA chemistry†

Juliana T. W. Tong, ORCID logo ab   Iman Kavianinia, ORCID logo acb   Scott A. Ferguson, ORCID logo d   Gregory M. Cook,d   Paul W. R. Harris ORCID logo *acb  and  Margaret A. Brimble ORCID logo *acb  

* Corresponding authors

a School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland 1010, New Zealand
E-mail: m.brimble@auckland.ac.nz

b Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3 Symonds Street, Auckland, New Zealand

c School of Biological Sciences, The University of Auckland, 3A Symonds Street, Auckland 1010, New Zealand

d Department of Microbiology and Immunology, School of Medical Sciences, University of Otago, 720 Cumberland Street, Dunedin 9054, New Zealand

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.

Graphical abstract: Synthesis of paenipeptin C′ analogues employing solution-phase CLipPA chemistry

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Article information

DOI
https://doi.org/10.1039/D0OB00950D
Article type
Communication
Submitted
08 May 2020
Accepted
26 May 2020
First published
26 May 2020

Org. Biomol. Chem., 2020,18, 4381-4385

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

J. T. W. Tong, I. Kavianinia, S. A. Ferguson, G. M. Cook, P. W. R. Harris and M. A. Brimble, Org. Biomol. Chem., 2020, 18, 4381 DOI: 10.1039/D0OB00950D

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