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Issue 37, 2018
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Genome mining, isolation, chemical synthesis and biological evaluation of a novel lanthipeptide, tikitericin, from the extremophilic microorganism Thermogemmatispora strain T81

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Abstract

Genome mining of the New Zealand extremophilic microorganism Thermogemmatispora strain T81 indicated the presence of biosynthetic machinery to produce several different peptidic natural products. Solid-phase culture of T81 led to the isolation of tikitericin 1, a new lanthipeptide characterised by four (methyl)lanthionine bridges. The mass-guided isolation and structural elucidation of tikitericin 1 is described together with its total synthesis via Fmoc-solid-phase peptide synthesis (SPPS). The key non-canonical (methyl)lanthionine residues were synthesised in solution phase via an improved synthetic route and subsequently assembled to construct the peptide backbone using Fmoc-SPPS. N-Terminal truncated analogues of tikitericin (2–5) were also prepared in order to evaluate the contribution of each sequential ring of the polycyclic lanthipeptide to the antibacterial activity.

Graphical abstract: Genome mining, isolation, chemical synthesis and biological evaluation of a novel lanthipeptide, tikitericin, from the extremophilic microorganism Thermogemmatispora strain T81

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Publication details

The article was received on 17 May 2018, accepted on 19 Aug 2018 and first published on 20 Aug 2018


Article type: Edge Article
DOI: 10.1039/C8SC02170H
Citation: Chem. Sci., 2018,9, 7311-7317
  • Open access: Creative Commons BY-NC license
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    Genome mining, isolation, chemical synthesis and biological evaluation of a novel lanthipeptide, tikitericin, from the extremophilic microorganism Thermogemmatispora strain T81

    B. Xu, E. J. Aitken, B. P. Baker, C. A. Turner, J. E. Harvey, M. B. Stott, J. F. Power, Paul W. R. Harris, R. A. Keyzers and M. A. Brimble, Chem. Sci., 2018, 9, 7311
    DOI: 10.1039/C8SC02170H

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      [Original citation] - Published by The Royal Society of Chemistry.

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