Ribosomally derived lipopeptides containing distinct fatty acyl moieties
International audience Lipopeptides represent a large group of microbial natural products that include important antibacterial and antifungal drugs and some of the most-powerful known biosurfactants. The vast majority of lipopeptides comprise cyclic peptide backbones N-terminally equipped with vario...
Published in: | Proceedings of the National Academy of Sciences |
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ftinstpasteur:oai:HAL:pasteur-03526529v1 2023-05-15T15:07:17+02:00 Ribosomally derived lipopeptides containing distinct fatty acyl moieties Hubrich, Florian Bösch, Nina, Chepkirui, Clara Morinaka, Brandon, Rust, Michael Gugger, Muriel Robinson, Serina, Vagstad, Anna, Piel, Jörn Eidgenössische Technische Hochschule - Swiss Federal Institute of Technology Zürich (ETH Zürich) National University of Singapore (NUS) Collection des Cyanobactéries Institut Pasteur Paris (IP)-Université Paris Cité (UPCité) Swiss Federal Insitute of Aquatic Science and Technology Dübendorf (EAWAG) We are grateful for financial support (F.H. for financial support by the Vontobel Foundation, S.L.R. for financial support by the ETH Zürich Postdoctoral Fellowship 20-1 FEL-07 , and J.P. for financial support by the Swiss National Science Foundation (SNSF) National Research Program 72 “Antimicrobial resistance,” 407240_167051 ). 2022-01-13 https://hal-pasteur.archives-ouvertes.fr/pasteur-03526529 https://hal-pasteur.archives-ouvertes.fr/pasteur-03526529/document https://hal-pasteur.archives-ouvertes.fr/pasteur-03526529/file/e2113120119.full.pdf https://doi.org/10.1073/pnas.2113120119 en eng HAL CCSD National Academy of Sciences info:eu-repo/semantics/altIdentifier/doi/10.1073/pnas.2113120119 info:eu-repo/semantics/altIdentifier/pmid/35027450 pasteur-03526529 https://hal-pasteur.archives-ouvertes.fr/pasteur-03526529 https://hal-pasteur.archives-ouvertes.fr/pasteur-03526529/document https://hal-pasteur.archives-ouvertes.fr/pasteur-03526529/file/e2113120119.full.pdf doi:10.1073/pnas.2113120119 PUBMED: 35027450 http://creativecommons.org/licenses/by-nc-nd/ info:eu-repo/semantics/OpenAccess CC-BY-NC-ND ISSN: 0027-8424 EISSN: 1091-6490 Proceedings of the National Academy of Sciences of the United States of America https://hal-pasteur.archives-ouvertes.fr/pasteur-03526529 Proceedings of the National Academy of Sciences of the United States of America, 2022, 119 (3), pp.e2113120119. ⟨10.1073/pnas.2113120119⟩ RiPPs natural products peptides N-acylation biosynthesis [SDV]Life Sciences [q-bio] info:eu-repo/semantics/article Journal articles 2022 ftinstpasteur https://doi.org/10.1073/pnas.2113120119 2023-02-22T00:03:52Z International audience Lipopeptides represent a large group of microbial natural products that include important antibacterial and antifungal drugs and some of the most-powerful known biosurfactants. The vast majority of lipopeptides comprise cyclic peptide backbones N-terminally equipped with various fatty acyl moieties. The known compounds of this type are biosynthesized by nonribosomal peptide synthetases, giant enzyme complexes that assemble their products in a non–gene-encoded manner. Here, we report the genome-guided discovery of ribosomally derived, fatty-acylated lipopeptides, termed selidamides. Heterologous reconstitution of three pathways, two from cyanobacteria and one from an arctic, ocean-derived alphaproteobacterium, allowed structural characterization of the probable natural products and suggest that selidamides are widespread over various bacterial phyla. The identified representatives feature cyclic peptide moieties and fatty acyl units attached to (hydroxy)ornithine or lysine side chains by maturases of the GCN5-related N -acetyltransferase superfamily. In contrast to nonribosomal lipopeptides that are usually produced as congener mixtures, the three selidamides are selectively fatty acylated with C 10 , C 12 , or C 16 fatty acids, respectively. These results highlight the ability of ribosomal pathways to emulate products with diverse, nonribosomal-like features and add to the biocatalytic toolbox for peptide drug improvement and targeted discovery. Article in Journal/Newspaper Arctic Arctic Ocean Institut Pasteur: HAL Arctic Arctic Ocean Proceedings of the National Academy of Sciences 119 3 e2113120119 |
institution |
Open Polar |
collection |
Institut Pasteur: HAL |
op_collection_id |
ftinstpasteur |
language |
English |
topic |
RiPPs natural products peptides N-acylation biosynthesis [SDV]Life Sciences [q-bio] |
spellingShingle |
RiPPs natural products peptides N-acylation biosynthesis [SDV]Life Sciences [q-bio] Hubrich, Florian Bösch, Nina, Chepkirui, Clara Morinaka, Brandon, Rust, Michael Gugger, Muriel Robinson, Serina, Vagstad, Anna, Piel, Jörn Ribosomally derived lipopeptides containing distinct fatty acyl moieties |
topic_facet |
RiPPs natural products peptides N-acylation biosynthesis [SDV]Life Sciences [q-bio] |
description |
International audience Lipopeptides represent a large group of microbial natural products that include important antibacterial and antifungal drugs and some of the most-powerful known biosurfactants. The vast majority of lipopeptides comprise cyclic peptide backbones N-terminally equipped with various fatty acyl moieties. The known compounds of this type are biosynthesized by nonribosomal peptide synthetases, giant enzyme complexes that assemble their products in a non–gene-encoded manner. Here, we report the genome-guided discovery of ribosomally derived, fatty-acylated lipopeptides, termed selidamides. Heterologous reconstitution of three pathways, two from cyanobacteria and one from an arctic, ocean-derived alphaproteobacterium, allowed structural characterization of the probable natural products and suggest that selidamides are widespread over various bacterial phyla. The identified representatives feature cyclic peptide moieties and fatty acyl units attached to (hydroxy)ornithine or lysine side chains by maturases of the GCN5-related N -acetyltransferase superfamily. In contrast to nonribosomal lipopeptides that are usually produced as congener mixtures, the three selidamides are selectively fatty acylated with C 10 , C 12 , or C 16 fatty acids, respectively. These results highlight the ability of ribosomal pathways to emulate products with diverse, nonribosomal-like features and add to the biocatalytic toolbox for peptide drug improvement and targeted discovery. |
author2 |
Eidgenössische Technische Hochschule - Swiss Federal Institute of Technology Zürich (ETH Zürich) National University of Singapore (NUS) Collection des Cyanobactéries Institut Pasteur Paris (IP)-Université Paris Cité (UPCité) Swiss Federal Insitute of Aquatic Science and Technology Dübendorf (EAWAG) We are grateful for financial support (F.H. for financial support by the Vontobel Foundation, S.L.R. for financial support by the ETH Zürich Postdoctoral Fellowship 20-1 FEL-07 , and J.P. for financial support by the Swiss National Science Foundation (SNSF) National Research Program 72 “Antimicrobial resistance,” 407240_167051 ). |
format |
Article in Journal/Newspaper |
author |
Hubrich, Florian Bösch, Nina, Chepkirui, Clara Morinaka, Brandon, Rust, Michael Gugger, Muriel Robinson, Serina, Vagstad, Anna, Piel, Jörn |
author_facet |
Hubrich, Florian Bösch, Nina, Chepkirui, Clara Morinaka, Brandon, Rust, Michael Gugger, Muriel Robinson, Serina, Vagstad, Anna, Piel, Jörn |
author_sort |
Hubrich, Florian |
title |
Ribosomally derived lipopeptides containing distinct fatty acyl moieties |
title_short |
Ribosomally derived lipopeptides containing distinct fatty acyl moieties |
title_full |
Ribosomally derived lipopeptides containing distinct fatty acyl moieties |
title_fullStr |
Ribosomally derived lipopeptides containing distinct fatty acyl moieties |
title_full_unstemmed |
Ribosomally derived lipopeptides containing distinct fatty acyl moieties |
title_sort |
ribosomally derived lipopeptides containing distinct fatty acyl moieties |
publisher |
HAL CCSD |
publishDate |
2022 |
url |
https://hal-pasteur.archives-ouvertes.fr/pasteur-03526529 https://hal-pasteur.archives-ouvertes.fr/pasteur-03526529/document https://hal-pasteur.archives-ouvertes.fr/pasteur-03526529/file/e2113120119.full.pdf https://doi.org/10.1073/pnas.2113120119 |
geographic |
Arctic Arctic Ocean |
geographic_facet |
Arctic Arctic Ocean |
genre |
Arctic Arctic Ocean |
genre_facet |
Arctic Arctic Ocean |
op_source |
ISSN: 0027-8424 EISSN: 1091-6490 Proceedings of the National Academy of Sciences of the United States of America https://hal-pasteur.archives-ouvertes.fr/pasteur-03526529 Proceedings of the National Academy of Sciences of the United States of America, 2022, 119 (3), pp.e2113120119. ⟨10.1073/pnas.2113120119⟩ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.1073/pnas.2113120119 info:eu-repo/semantics/altIdentifier/pmid/35027450 pasteur-03526529 https://hal-pasteur.archives-ouvertes.fr/pasteur-03526529 https://hal-pasteur.archives-ouvertes.fr/pasteur-03526529/document https://hal-pasteur.archives-ouvertes.fr/pasteur-03526529/file/e2113120119.full.pdf doi:10.1073/pnas.2113120119 PUBMED: 35027450 |
op_rights |
http://creativecommons.org/licenses/by-nc-nd/ info:eu-repo/semantics/OpenAccess |
op_rightsnorm |
CC-BY-NC-ND |
op_doi |
https://doi.org/10.1073/pnas.2113120119 |
container_title |
Proceedings of the National Academy of Sciences |
container_volume |
119 |
container_issue |
3 |
container_start_page |
e2113120119 |
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1766338817832255488 |