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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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
Issue number37
Early online date31 Jul 2015
Publication statusPublished - 2015

Bibliographical note

KK, MJ, RE and HD are grateful for financial support through the Leverhulme Trust-Royal Society Africa award (AA090088). MJ, RE, HD, JT and KH thank EU FP7 for financial support (contract no. 312184). HD thanks the School of Natural and
Computing Sciences, University of Aberdeen, for a PhD scholarship to XLW. PCD gratefully acknowledges grants from the National Institute of Health (GM097509 and GMS10RR029121). We thank the Bruker Therapeutic Discovery Mass Spectrometry Center for recording the MSn spectra.


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