Genome mining, isolation, chemical synthesis and biological evaluation of a novel lanthipeptide, tikitericin, from the extremophilic microorganism Thermogemmatispora strain T81
| Autor: | Emma J. Aitken, Paul W. R. Harris, Benjamin P. Baker, Robert A. Keyzers, Claire A. Turner, Jean F. Power, Margaret A. Brimble, Joanne E. Harvey, Matthew B. Stott, Buzhe Xu |
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| Rok vydání: | 2018 |
| Předmět: |
0301 basic medicine
Strain (chemistry) Stereochemistry Microorganism Total synthesis General Chemistry 010402 general chemistry Isolation (microbiology) 01 natural sciences Chemical synthesis 0104 chemical sciences 03 medical and health sciences chemistry.chemical_compound 030104 developmental biology chemistry Peptide synthesis Antibacterial activity Lanthionine |
| Zdroj: | Chemical Science. 9:7311-7317 |
| ISSN: | 2041-6539 2041-6520 |
| DOI: | 10.1039/c8sc02170h |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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