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Total synthesis of rosette inhibitor IOR allows its functional analysis and evaluation of sulfonolipid-based chemical probes

ABSTRACT: The predatory choanoflagellate Salpingoeca rosetta has emerged as important model systems to study the evolution of multicellularity and chemical origin of bacterial-eukaryote communication mechanisms. In this study we elaborated on the function and possible proteogenic binding partners of the bacterial sulfonolipid IOR-1A, which serves as bacterial inhibitor of rosette formation in S. rosetta. To study the function of IOR-1A, a new, modular and scalable total synthesis of IOR-1A (six steps, 30% overall yield) was developed, which features a decarboxylative cross-coupling reaction of a desymmetrized tartaric acid derivative carrying a protected sulfonic acid moiety with an alkyl zink reagents of choice. Synthesis of twelve IOR derivates, including fluorescent and photoaffinity-based probes, allowed to determine the abundance of IOR-1A, evaluation of structure-activity relations, localization studies within S. rosetta and de novo chemical proteomic identification of IOR-binding proteins in bacteria and S. rosetta. The combined results will catalyse future studies aiming at deciphering the biochemical basis of cell differentiation processes within rosette formation of S. rosetta.

INSTRUMENT(S): Q Exactive Plus, Q Exactive HF

ORGANISM(S): Echinicola Pacifica Algoriphagus Machipongonensis Salpingoeca Rosetta

SUBMITTER: Thomas Krüger

LAB HEAD: Axel A. Brakhage

PROVIDER: PXD034064 | Pride | 2022-08-29

REPOSITORIES: Pride

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Total Synthesis and Functional Evaluation of IORs, Sulfonolipid-based Inhibitors of Cell Differentiation in Salpingoeca rosetta.

Raguž Luka L Peng Chia-Chi CC Rutaganira Florentine U N FUN Krüger Thomas T Stanišić Aleksa A Jautzus Theresa T Kries Hajo H Kniemeyer Olaf O Brakhage Axel A AA King Nicole N Beemelmanns Christine C

Angewandte Chemie (International ed. in English) 20220905 41

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, inc ...[more]

PMID: 35901418

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