Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 41, Pages 16271-16278Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b04183
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Funding
- National Institutes of Health [1DP2-CA186575]
- Burroughs Wellcome Foundation [1016720]
- Camille and Henry Dreyfus Foundation [TC-17-011]
- Yale University
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Isocyanide functional groups can be found in a variety of natural products. Rhabduscin is one such isocyanide-functionalized immunosuppressant produced in Xenorhabdus and Photorhabdus gammaproteobacterial pathogens, and deletion of its biosynthetic gene cluster inhibits virulence in an invertebrate animal infection model. Here, we characterized the first opine-glycopeptide class of natural products termed rhabdoplanins, and strikingly, these molecules are spontaneously produced from rhabduscin via an unprecedented multicomponent Ugi-like reaction sequence in nature. The rhabdoplanins also represent new lead G protein-coupled receptor (GPCR) agonists, stimulating the bombesin receptor subtype-3 (BB3) GPCR.
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