Photoaffinity probes for nematode pheromone receptor identification. Issue 1 (29th November 2019)

• Record Type: Journal Article
• Authors: Zhang, Ying K.; Reilly, Douglas K.; Yu, Jingfang; Srinivasan, Jagan; Schroeder, Frank C.
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 1(2019)
• Page Start: 36
• Page End: 40
• Publication Date: 2019-11-29
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob02099c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Identification of pheromone receptors plays a central role for uncovering signaling pathways that underlie chemical communication in animals. 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 .