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Alaninyl variants of the marine natural product halocyamine A and their antibacterial properties

Abstract : In an effort to explore the antibacterial potential of the marine natural product halocyamine A, a series of analogues including desbromo and alanine-substituted variants were synthesised and evaluated for biological activity against a panel of Gram-positive and –negative bacteria. The analogues were synthesisedby a combination of solid-phase peptide synthesis and ruthenium complex/ytterbium triflate catalysed hydroamidation chemistry. Single alanine substitutions ([Ala1]-halocyamine A and [Ala2]-halocyamine A) gave only modest increases in activity towards Gram-positive bacteria, while dialaninyl variants exhibited more potent activity with MIC values of 12.5–50 µM towards the Gram-positive bacteria S.aureus and E. faecalis. A lipophilic trityl-protected intermediate of [Ala2]-halocyamine was the most active against the Gram negative bacterium Escherichia coli.
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Hugo K.H. Fong, Melissa Cadelis, Jean Michel Brunel, Marie-Lise Bourguet-Kondracki, David Barker, et al.. Alaninyl variants of the marine natural product halocyamine A and their antibacterial properties. Tetrahedron, Elsevier, 2018, 74 (48), pp.6929-6938. ⟨10.1016/jet.2018.10.021⟩. ⟨hal-02056446⟩

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