Ribosomally derived lipopeptides containing distinct fatty acyl moieties
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....
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National Academy of Sciences, USA
2022
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Online Access: | https://doi.org/10.1073/pnas.2113120119 |
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fteawag:oai:dora:eawag_24349 2024-09-15T17:53:56+00:00 Ribosomally derived lipopeptides containing distinct fatty acyl moieties Hubrich, Florian Bösch, Nina M. Chepkirui, Clara Morinaka, Brandon I. Rust, Michael Gugger, Muriel Robinson, Serina L. Vagstad, Anna L. Piel, Jörn 2022 https://doi.org/10.1073/pnas.2113120119 eng eng National Academy of Sciences, USA Proceedings of the National Academy of Sciences of the United States of America PNAS--Proc. Natl. Acad. Sci. U. S. A.--journals:3061--0027-8424--1091-6490 eawag:24349 doi:10.1073/pnas.2113120119 scopus: 2-s2.0-85123076989 pmid: 35027450 journal id: journals:3061 issn: 0027-8424 e-issn: 1091-6490 ut: 000748781000011 RiPPs natural products peptides N-acylation biosynthesis Journal Article Text 2022 fteawag https://doi.org/10.1073/pnas.2113120119 2024-08-05T03:04:28Z 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 Ocean DORA Eawag Proceedings of the National Academy of Sciences 119 3 |
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English |
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RiPPs natural products peptides N-acylation biosynthesis |
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RiPPs natural products peptides N-acylation biosynthesis Hubrich, Florian Bösch, Nina M. Chepkirui, Clara Morinaka, Brandon I. Rust, Michael Gugger, Muriel Robinson, Serina L. Vagstad, Anna L. Piel, Jörn Ribosomally derived lipopeptides containing distinct fatty acyl moieties |
topic_facet |
RiPPs natural products peptides N-acylation biosynthesis |
description |
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. |
format |
Article in Journal/Newspaper |
author |
Hubrich, Florian Bösch, Nina M. Chepkirui, Clara Morinaka, Brandon I. Rust, Michael Gugger, Muriel Robinson, Serina L. Vagstad, Anna L. Piel, Jörn |
author_facet |
Hubrich, Florian Bösch, Nina M. Chepkirui, Clara Morinaka, Brandon I. Rust, Michael Gugger, Muriel Robinson, Serina L. Vagstad, Anna L. 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 |
National Academy of Sciences, USA |
publishDate |
2022 |
url |
https://doi.org/10.1073/pnas.2113120119 |
genre |
Arctic Ocean |
genre_facet |
Arctic Ocean |
op_relation |
Proceedings of the National Academy of Sciences of the United States of America PNAS--Proc. Natl. Acad. Sci. U. S. A.--journals:3061--0027-8424--1091-6490 eawag:24349 doi:10.1073/pnas.2113120119 scopus: 2-s2.0-85123076989 pmid: 35027450 journal id: journals:3061 issn: 0027-8424 e-issn: 1091-6490 ut: 000748781000011 |
op_doi |
https://doi.org/10.1073/pnas.2113120119 |
container_title |
Proceedings of the National Academy of Sciences |
container_volume |
119 |
container_issue |
3 |
_version_ |
1810430069074558976 |