Poster Presentation 8th Modern Solid Phase Peptide Synthesis & Its Applications Symposium 2022

The Total Chemical Synthesis and Biological Evaluation of the Cationic Antimicrobial Peptide, Brevicidine (#134)

Dennise M Palpal-latoc 1 , Alan Cameron 1 , Paul Harris 1 , Margaret Brimble 1
  1. Chemistry, The University of Auckland, Auckland, New Zealand

Antimicrobial resistance has become a significant threat to human health and it demands urgent action to develop new therapeutic agents with novel mechanisms of action.1 Recently, a new cationic non-ribosomal peptide (CNRP), brevicidine, was discovered from Brevibacillus laterosporus through a global-genome mining approach.2 Brevicidine exhibits potent antimicrobial activity toward Gram-negative bacteria, including colistin-resistant Escherichia coli, and a low risk of resistance development. Herein, we report the first total synthesis of brevicidine via an efficient and high-yielding synthetic pathway, employing both solid-phase synthesis and solution-phase macrolactamization. The crucial depsipeptide bond of the macrolactone ring of brevicidine was established on-resin between the side-chain hydroxy group of Thr9 with Alloc-Ser(tBu)-OH. A conserved glycine residue within the lactone macrocycle was exploited for the initial immobilisation onto the hyper acid-labile 2-chlorotrityl chloride resin, subsequently enabling an efficient solution-phase macrocyclization to yield brevicidine in 10% overall yield (with respect to resin loading). A biological evaluation against both Gram-positive and Gram-negative bacteria demonstrated that synthetic brevicidine possessed a potent and selective antimicrobial activity toward Gram-negative bacteria, in agreement with the isolated compound.

  1. Aminov, R. I. A Brief History of the Antibiotic Era: Lessons Learned and Challenges for the Future. Front. Microbiol. 2010, 1. https://doi.org/10.3389/fmicb.2010.00134.
  2. Li, Y.-X.; Zhong, Z.; Zhang, W.-P.; Qian, P.-Y. Discovery of Cationic Nonribosomal Peptides as Gram-Negative Antibiotics through Global Genome Mining. Nat. Commun. 2018, 9 (1), 1–9. https://doi.org/10.1038/s41467-018-05781-6.