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Photoaffinity probes for nematode pheromone receptor identification

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Abstract

Identification of pheromone receptors plays a central role for uncovering signaling pathways that underlie chemical communication in animals. Here, we describe the synthesis and bioactivity of photoaffinity probes for the ascaroside ascr#8, a sex-pheromone of the model nematode, Caenorhabditis elegans. Structure–activity studies guided incorporation of alkyne- and diazirine-moieties and revealed that addition of functionality in the sidechain of ascr#8 was well tolerated, whereas modifications to the ascarylose moiety resulted in loss of biological activity. Our study will guide future probe design and provides a basis for pheromone receptor identification via photoaffinity labeling in C. elegans.

Graphical abstract: Photoaffinity probes for nematode pheromone receptor identification

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Publication details

The article was received on 28 Sep 2019, accepted on 22 Nov 2019 and first published on 22 Nov 2019


Article type: Communication
DOI: 10.1039/C9OB02099C
Org. Biomol. Chem., 2020, Advance Article

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    Photoaffinity probes for nematode pheromone receptor identification

    Y. K. Zhang, D. K. Reilly, J. Yu, J. Srinivasan and F. C. Schroeder, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02099C

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