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Photoaffinity probes for nematode pheromone receptor identification.

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.

SUBMITTER: Zhang YK

PROVIDER: S-EPMC6961461 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Photoaffinity probes for nematode pheromone receptor identification.

Zhang Ying K YK Reilly Douglas K DK Yu Jingfang J Srinivasan Jagan J Schroeder Frank C FC

Organic & biomolecular chemistry 20191201 1

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 t ...[more]

PMID: 31781713

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