Abstract
The cosmopolitan marine Roseobacter clade is of global biogeochemical importance. Members of this clade produce sulfur-containing amino lipids (SALs) of importance for biofilm formation and marine surface colonization processes. Despite their physiological importance and abundance, SALs have only been explored through genomic mining approaches and lipidomic studies based on mass spectrometry, which left the relative and absolute structures of SALs unresolved hindering progress in biochemical and functional investigations. Here, we report the structural revision of a new group of SALs, which we named cysteinolides, using a combination of analytical techniques, isolation and degradation experiments and total synthetic efforts. Contrary to the previously proposed homotaurine-based structures, cysteinolides are composed of an N,O-acylated cysteinolic acid-containing head group carrying various different (α‑hydroxy) carboxylic acids. We performed the first validated targeted-network based analysis, which allowed us to map the distribution and structural diversity of cysteinolides across bacterial lineages. Beyond offering structural insights, our research provides SAL standards and validated analytical data. This information holds significance for forthcoming investigations into bacterial sulfonolipid metabolism and biogeochemical nutrient cycling within marine environments.
Original language | English |
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Article number | e202401195 |
Journal | Angewandte Chemie (International Edition) |
Early online date | 26 Mar 2024 |
DOIs | |
Publication status | E-pub ahead of print - 26 Mar 2024 |
Bibliographical note
Acknowledgements:We would also like to thank Heike Heinecke (Leibniz-HKI) for measurement of NMR spectra, Nina Messerschmidt (Leibniz-HKI) for preliminary cytotoxic and antiproliferative assays, and Nils Dormanns for providing strain Ruegeria meonggei ND-6.PRM thanks the Studienstiftung des deutschen Volkes for financial support during his study program. CB greatly acknowledges funding from the European Union’s Horizon 2020 research and innovation program (ERC Grant number: 802736, MORPHEUS). RG and YC acknowledge the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation programme (grant agreement no. 726116).This work was supported by the Deutsche Forschungsgemeinschaft, SFB 1127/3 ChemBioSys project no. 239748522 (to OW, CH, and CB).
Copyright:
© 2024 Wiley‐VCH GmbH.
Keywords
- total synthesis
- Natural Products
- sulfonolipids
- cysteinolides
- Roseobacter