Total Synthesis of Laspartomycin C and Characterization of Its Antibacterial Mechanism of Action

Laurens H J Kleijn, Sabine F. Oppedijk, Peter T Hart, Roel van Harten, Leah A. Martin-Visscher, Johan Kemmink, Eefjan Breukink, Nathaniel I. Martin*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

Laspartomycin C is a lipopeptide antibiotic with activity against a range of Gram-positive bacteria including drug-resistant pathogens. We report the first total synthesis of laspartomycin C as well as a series of structural variants. Laspartomycin C was found to specifically bind undecaprenyl phosphate (C55-P) and inhibit formation of the bacterial cell wall precursor lipid II. While several clinically used antibiotics target the lipid II pathway, there are no approved drugs that act on its C55-P precursor.

Original languageEnglish
Pages (from-to)3569-3574
Number of pages6
JournalJournal of Medicinal Chemistry
Volume59
Issue number7
DOIs
Publication statusPublished - 11 Mar 2016

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