2. Academic Validation
  3. A Concise Synthetic Strategy Towards the Novel Calcium-dependent Lipopeptide Antibiotic, Malacidin A and Analogues

A Concise Synthetic Strategy Towards the Novel Calcium-dependent Lipopeptide Antibiotic, Malacidin A and Analogues

  • Front Chem. 2021 Aug 4;9:687875. doi: 10.3389/fchem.2021.687875.
Nadiia Kovalenko 1,  Georgina K Howard 1,  Jonathan A Swain 1,  Yann Hermant 1,  Alan J Cameron 1 2 3,  Gregory M Cook 3 4,  Scott A Ferguson 4,  Louise A Stubbing 1,  Paul W R Harris 1 2 3,  Margaret A Brimble 1 2 3
Affiliations

Affiliations

  • 1 School of Chemical Sciences, The University of Auckland, Auckland, New Zealand.
  • 2 School of Biological Sciences, The University of Auckland, Auckland, New Zealand.
  • 3 Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, Auckland, New Zealand.
  • 4 Department of Microbiology and Immunology, School of Biomedical Sciences, University of Otago, Dunedin, New Zealand.
PMID: 34422759 DOI: 10.3389/fchem.2021.687875
Abstract

Malacidin A is a novel calcium-dependent Lipopeptide antibiotic with excellent activity against Gram-positive pathogens. Herein, a concise and robust synthetic route toward malacidin A is reported, employing 9-fluorenylmethoxycarbonyl solid-phase peptide synthesis of a linear precursor, including late-stage incorporation of the lipid tail, followed by solution-phase cyclization. The versatility of this synthetic strategy was further demonstrated by synthesis of a diastereomeric variant of malacidin A and a small library of simplified analogues with variation of the lipid moiety.

Keywords

antibiotic; antimicrobial; calcium-dependent; lipopeptide; solid-phase peptide synthesis.

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