A New Family of Rigid Dienone Musks Challenges the Perceptive Range of the Human Olfactory Receptor OR5AN1

Autor:	Yue Zou, Jie Liu, Sereina Riniker, Lijun Zhou, Stephanie M. Linker, Vera Hürlimann, Carmen Esposito, Roger Emter, Philip Kraft, Quanrui Wang, Andreas Natsch
Rok vydání:	2020
Předmět:	Olfactory receptor 010405 organic chemistry Stereochemistry Chemistry Organic Chemistry Alkylation 010402 general chemistry 01 natural sciences 0104 chemical sciences medicine.anatomical_structure Cascade reaction Intramolecular force Nitro medicine Lewis acids and bases Receptor Isomerization
Zdroj:	Synlett. 31:972-976
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-0040-1708009
Popis:	A new family of dienone musks was discovered by alkylation of different aldehydes with but-3-en-1-yn-1-yllithium and subsequent domino reaction of a Saucy–Marbet transfer vinylation–Claisen rearrangement with an intramolecular Diels–Alder reaction, and concluding Lewis acid catalyzed double-bond isomerization. The newly synthesized dienone structures possess pleasant musk odors displaying fatty, slightly fruity and green facets. Although the dienone musks were predicted in silico to bind to the OR5AN1 receptor based on QM/MM calculations, they were found to be inactive in the in vitro assay. The latter results suggest that the OR5AN1 receptor is not the prime musk receptor but primarily responsible for the animalic character of certain macrocyclic ketones and nitro musks.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c3136f2a2101b017fc0c5a81597046b1 https://doi.org/10.1055/s-0040-1708009 Zobrazit plný text záznamu