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

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Streptomyces
Bioinformatics
Computational Biology
Ghana
nuclear magnetic resonance
biosynthesis
Biosynthesis
Multigene Family
Carboxylic Acids
carboxylic acids
genes
bacteria
Nuclear magnetic resonance spectroscopy
peptides
isolation
soils
Bacteria
Magnetic Resonance Spectroscopy
Soil
Genes

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Legonaridin, a new member of linaridin RiPP from a Ghanaian Streptomyces Isolate. / Rateb, Mostafa E; Zhai, Yin; Ehrner, Emmanuelle ; Rath, Christopher; Wang, Xiaoling; Tabudravu, Jioji; Ebel, Rainer Peter; Bibb, Mervin; Kyeremeh, Kwaku; Dorrestein, Pieter; Hong, Kui; Jaspars, Marcel; Deng, Hai.

In: Organic & Biomolecular Chemistry, Vol. 13, No. 37, 2015, p. 9585-9592.

Research output: Contribution to journalArticle

Rateb, ME, Zhai, Y, Ehrner, E, Rath, C, Wang, X, Tabudravu, J, Ebel, RP, 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, vol. 13, no. 37, pp. 9585-9592. https://doi.org/10.1039/C5OB01269D
Rateb, Mostafa E ; Zhai, Yin ; Ehrner, Emmanuelle ; Rath, Christopher ; Wang, Xiaoling ; Tabudravu, Jioji ; Ebel, Rainer Peter ; Bibb, Mervin ; Kyeremeh, Kwaku ; Dorrestein, Pieter ; Hong, Kui ; Jaspars, Marcel ; Deng, Hai. / Legonaridin, a new member of linaridin RiPP from a Ghanaian Streptomyces Isolate. In: Organic & Biomolecular Chemistry. 2015 ; Vol. 13, No. 37. pp. 9585-9592.
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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.",
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note = "Acknowledgements 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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AU - Zhai, Yin

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AU - Rath, Christopher

AU - Wang, Xiaoling

AU - Tabudravu, Jioji

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AU - Hong, Kui

AU - Jaspars, Marcel

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N1 - Acknowledgements 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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N2 - 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.

AB - 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.

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