The choanoflagellate Salpingoeca rosetta is an important model system to study the evolution of
multicellularity. In this study we developed a new, modular, and scalable synthesis of sulfonolipid IOR-1A (six steps,
27% overall yield), which acts as bacterial inhibitor of rosette formation in S. rosetta. The synthesis features a
decarboxylative cross-coupling reaction of a sulfonic acid-containing tartaric acid derivative with alkyl zinc reagents.
Synthesis of 15 modified IOR-1A derivatives, including fluorescent and photoaffinity-based probes, allowed
quantification of IOR-1A, localization studies within S. rosetta cells, and evaluation of structure-activity relations. In a
proof of concept study, an inhibitory bifunctional probe was employed in proteomic profiling studies, which allowed to
deduce binding partners in bacteria and S. rosetta. These results showcase the power of synthetic chemistry to decipher the biochemical basis of cell differentiation processes within S. rosetta.
| Identifer | oai:union.ndltd.org:DRESDEN/oai:qucosa:de:qucosa:94793 |
| Date | 10 December 2024 |
| Creators | Raguž, Luka, Peng, Chia-Chi, Rutaganira, Florentine U. N., Krüger, Thomas, Stanišić, Aleksa, Jautzus, Theresa, Kries, Hajo, Kniemeyer, Olaf, Brakhage, Axel A., King, Nicole, Beemelmanns, Christine |
| Publisher | Wiley-VCH |
| Source Sets | Hochschulschriftenserver (HSSS) der SLUB Dresden |
| Language | English |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, doc-type:article, info:eu-repo/semantics/article, doc-type:Text |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | 1433-7851, 1521-3773, 10.1002/anie.202209105 |
Page generated in 0.0128 seconds