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Issue 1, 2020
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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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Article information


Submitted
28 Sep 2019
Accepted
22 Nov 2019
First published
22 Nov 2019

Org. Biomol. Chem., 2020,18, 36-40
Article type
Communication

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, 18, 36
DOI: 10.1039/C9OB02099C

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