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

Mostafa Rateb, Yin Zhai, Emmanuelle Ehrner, Christopher M. Rath, Xiaoling Wang, Jioji Tabudravu, Rainer Ebel, Mervin Bibb, Kwaku Kyeremeh, Pieter C. 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 those of cypemycin and SGR-1832. Consistent with bioinformatics and peptidogenomics analyses, 1 has a total of nine post-modifications, 8 dehydrobutyrine residues and a 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 that NMR spectroscopy is used to establish the 2-D structure of a linaridin RiPP.

Original languageEnglish
Pages (from-to)9585-9592
JournalOrganic & Biomolecular Chemistry
Issue number37
DOIs
Publication statusPublished - 7 Oct 2015
Externally publishedYes

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