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

Mostafa E. 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

doi:10.1039/C5OB01269D

Legonaridin, a new member of linaridin RiPP from a Ghanaian Streptomyces isolate†

Mostafa E. Rateb,^ab Yin Zhai,^c Emmanuelle Ehrner,^a Christopher M. Rath,^d Xiaoling Wang,^a Jioji Tabudravu,^a Rainer Ebel,^a Mervin Bibb,^e Kwaku Kyeremeh,^f Pieter C. Dorrestein,^dg Kui Hong,*^c Marcel Jaspars*^a and Hai Deng*^a

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* Corresponding authors

^a Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Aberdeen AB24 3UE Scotland, UK
E-mail: h.deng@abdn.ac.uk, m.jaspars@abdn.ac.uk

^b Pharmacognosy Department, School of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt

^c Key Laboratory of Combinatory Biosynthesis and Drug Discovery, School of Pharmaceutical Sciences, Wuhan University, 185 East Lake Road, Wuhan 430071, China
E-mail: kuihong31@whu.edu.cn

^d Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, La Jolla, California, USA

^e Department of Molecular Microbiology, John Innes Centre, Norwich NR4 7UH, UK

^f Department of Chemistry, FGO Torto Building, University of Ghana, Legon, Ghana

^g Department of Pharmacology and Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California, USA

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.

Organic & Biomolecular Chemistry

Legonaridin, a new member of linaridin RiPP from a Ghanaian Streptomyces isolate†

Abstract

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