Structure Revision of a Widespread Marine Sulfonolipid Class Based on Isolation and Total Synthesis.

Autor: Roman D; Chemical Biology of Microbe-Host Interactions, Leibniz Institute for Natural Product Research and Infection Biology-Hans Knöll Institute (HKI), Beutenbergstrasse 11 A, 07745, Jena, Germany.; Anti-Infectives from Microbiota Helmholtz Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI) Campus E8.1, 66123, Saarbrücken, Germany., Meisinger P; Chemical Biology of Microbe-Host Interactions, Leibniz Institute for Natural Product Research and Infection Biology-Hans Knöll Institute (HKI), Beutenbergstrasse 11 A, 07745, Jena, Germany.; Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology-Hans Knöll Institute (HKI), Beutenbergstrasse 11 A, 07745, Jena, Germany., Guillonneau R; Nantes Université, CNRS, US2B, UMR 6286, F-44000, Nantes, France., Peng CC; Chemical Biology of Microbe-Host Interactions, Leibniz Institute for Natural Product Research and Infection Biology-Hans Knöll Institute (HKI), Beutenbergstrasse 11 A, 07745, Jena, Germany.; Anti-Infectives from Microbiota Helmholtz Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI) Campus E8.1, 66123, Saarbrücken, Germany., Peltner LK; Department of Pharmaceutical/Medicinal Chemistry Institute of Pharmacy-, Friedrich-Schiller-University Jena, Philosophenweg 14, 07743, Jena, Germany., Jordan PM; Department of Pharmaceutical/Medicinal Chemistry Institute of Pharmacy-, Friedrich-Schiller-University Jena, Philosophenweg 14, 07743, Jena, Germany., Haensch V; Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology-Hans Knöll Institute (HKI), Beutenbergstrasse 11 A, 07745, Jena, Germany., Götze S; Anti-Infectives from Microbiota Helmholtz Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI) Campus E8.1, 66123, Saarbrücken, Germany., Werz O; Department of Pharmaceutical/Medicinal Chemistry Institute of Pharmacy-, Friedrich-Schiller-University Jena, Philosophenweg 14, 07743, Jena, Germany., Hertweck C; Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology-Hans Knöll Institute (HKI), Beutenbergstrasse 11 A, 07745, Jena, Germany.; Institute of Microbiology-, Friedrich-Schiller-University Jena, 07743, Jena, Germany., Chen Y; School of Biosciences, University of Birmingham, Edgbaston, B15 2TT, United Kingdom., Beemelmanns C; Chemical Biology of Microbe-Host Interactions, Leibniz Institute for Natural Product Research and Infection Biology-Hans Knöll Institute (HKI), Beutenbergstrasse 11 A, 07745, Jena, Germany.; Anti-Infectives from Microbiota Helmholtz Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI) Campus E8.1, 66123, Saarbrücken, Germany.; Saarland University, Campus E8.1, 66123, Saarbrücken, Germany.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Jun 03; Vol. 63 (23), pp. e202401195. Date of Electronic Publication: 2024 Apr 29.
DOI: 10.1002/anie.202401195
Abstrakt: The cosmopolitan marine Roseobacter clade is of global biogeochemical importance. Members of this clade produce sulfur-containing amino lipids (SALs) involved in biofilm formation and marine surface colonization processes. Despite their physiological relevance 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. Herein, 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 also 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 insight, 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.
(© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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