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Chem Sci. 2018 Aug 20;9(37):7311-7317. doi: 10.1039/c8sc02170h. eCollection 2018 Oct 7.

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

Author information

1
School of Chemical Sciences , 23 Symonds Street , Auckland 1010 , New Zealand . Email: m.brimble@auckland.ac.nz ; Tel: +64 9 9238259.
2
Maurice Wilkins Centre for Molecular Biodiscovery , The University of Auckland , Private Bag 92019 , Auckland 1142 , New Zealand . Email: rob.keyzers@vuw.ac.nz ; Tel: +64 4 4635117.
3
School of Chemical & Physical Sciences , The Centre for Biodiscovery , Victoria University of Wellington , PO Box 600 , Wellington 6140 , New Zealand.
4
School of Biological Sciences , University of Canterbury , Private Bag 4800 , Christchurch 8140 , New Zealand.
5
GNS Science , Private Bag 2000 , Taupō 3352 , New Zealand.
6
School of Biological Sciences , 23 Symonds Street , Auckland 1010 , New Zealand.

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.

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