| Registro completo |
| Provedor de dados: |
ArchiMer
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| País: |
France
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| Título: |
Unique Biosynthetic Pathway in Bloom-Forming Cyanobacterial Genus Microcystis Jointly Assembles Cytotoxic Aeruginoguanidines and Microguanidines
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| Autores: |
Pancrace, Claire
Ishida, Keishi
Briand, Enora
Pichi, Douglas Gatte
Weiz, Annika R.
Guljarnow, Arthur
Scalvenzi, Thibault
Sassoon, Nathalie
Hertweck, Christian
Dittmann, Elke
Gugger, Muriel
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| Data: |
2019-01
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| Ano: |
2019
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| Resumo: |
The cyanobacterial genus Microcystis is known to produce an elaborate array of structurally unique and biologically active natural products, including hazardous cyanotoxins. Cytotoxic aeruginoguanidines represent a yet unexplored family of peptides featuring a trisubstituted benzene unit and farnesylated arginine derivatives. In this study, we aimed at assigning these compounds to a biosynthetic gene cluster by utilizing biosynthetic attributes deduced from public genomes of Microcystis and the sporadic distribution of the metabolite in axenic strains of the Pasteur Culture Collection of Cyanobacteria. By integrating genome mining with untargeted metabolomics using liquid chromatography with mass spectrometry, we linked aeruginoguanidine (AGD) to a nonribosomal peptide synthetase gene cluster and coassigned a significantly smaller product to this pathway, microguanidine (MGD), previously only reported from two Microcystis blooms. Further, a new intermediate class of compounds named microguanidine amides was uncovered, thereby further enlarging this compound family. The comparison of structurally divergent AGDs and MGDs reveals an outstanding versatility of this biosynthetic pathway and provides insights into the assembly of the two compound subfamilies. Strikingly, aeruginoguanidines and microguanidines were found to be as widespread as the hepatotoxic microcystins, but the occurrence of both toxin families appeared to be mutually exclusive.
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| Tipo: |
Text
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| Idioma: |
Inglês
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| Identificador: |
https://archimer.ifremer.fr/doc/00481/59277/62216.pdf
DOI:10.1021/acschembio.8b00918
https://archimer.ifremer.fr/doc/00481/59277/
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| Editor: |
Amer Chemical Soc
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| Formato: |
application/pdf
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| Fonte: |
Acs Chemical Biology (1554-8929) (Amer Chemical Soc), 2019-01 , Vol. 14 , N. 1 , P. 67-75
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| Direitos: |
info:eu-repo/semantics/openAccess
restricted use
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