Legonaridin, a new member of linaridin RiPP from a Ghanaian Streptomyces Isolate

Mostafa E Rateb, Yin Zhai, Emmanuelle Ehrner, Christopher Rath, Xiaoling Wang, Jioji Tabudravu, Rainer Peter Ebel, Mervin Bibb, Kwaku Kyeremeh, Pieter Dorrestein, Kui Hong, Marcel Jaspars, Hai Deng

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Abstract

Linaridins are rare linear ribosomally-synthesized and post-translationally modified peptides (RiPPs) and only two, cypemycin and SGR-1832, in this family have been identified so far. Legonaridin 1 has been discovered as a new member of linaridins through chemical isolation, peptidogenomics, comprehensive 1- and 2-D NMR and advanced Marfey’s analyses from the soil bacterium Streptomyces sp. CT34, an isolate collected from Legon, Ghana. Bioinformatics analysis of the gene cluster suggested that the biosynthesis of legonaridin 1 is different from the ones for cypemycin and SGR-1832. Consistent with bioinformatics and peptidogenomics analyses, 1 has a total of nine post-modifications, 8 dehydrobutyrine residues and N,N-dimethylated N-terminus with a carboxylic acid at the C-terminus. Legonaridin 1 is structurally different from the two known linaridins comprising a new subfamily. This is the first time to use NMR spectroscopy to establish the 2-D structure of a linaridin RiPP.
Original languageEnglish
Pages (from-to)9585-9592
Number of pages8
JournalOrganic & Biomolecular Chemistry
Volume13
Issue number37
Early online date31 Jul 2015
DOIs
Publication statusPublished - 2015

ASJC Scopus subject areas

  • Organic Chemistry

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    Rateb, M. E., Zhai, Y., Ehrner, E., Rath, C., Wang, X., Tabudravu, J., Ebel, R. P., Bibb, M., Kyeremeh, K., Dorrestein, P., Hong, K., Jaspars, M., & Deng, H. (2015). Legonaridin, a new member of linaridin RiPP from a Ghanaian Streptomyces Isolate. Organic & Biomolecular Chemistry, 13(37), 9585-9592. https://doi.org/10.1039/C5OB01269D