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A New Family of Rigid Dienone Musks Challenges the Perceptive Range of the Human Olfactory Receptor OR5AN1
Synlett ( IF 1.7 ) Pub Date : 2020-03-24 , DOI: 10.1055/s-0040-1708009 Quanrui Wang 1 , Sereina Riniker 2 , Philip Kraft 3 , Jie Liu 1, 4 , Vera Hürlimann 3 , Roger Emter 3 , Andreas Natsch 3 , Carmen Esposito 2 , Stephanie M. Linker 2 , Yue Zou 4 , Lijun Zhou 4
Synlett ( IF 1.7 ) Pub Date : 2020-03-24 , DOI: 10.1055/s-0040-1708009 Quanrui Wang 1 , Sereina Riniker 2 , Philip Kraft 3 , Jie Liu 1, 4 , Vera Hürlimann 3 , Roger Emter 3 , Andreas Natsch 3 , Carmen Esposito 2 , Stephanie M. Linker 2 , Yue Zou 4 , Lijun Zhou 4
Affiliation
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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.
中文翻译：
新的刚性二烯酮麝香家族挑战人类嗅觉受体 OR5AN1 的感知范围
通过用but-3-en-1-yn-1-yllithium对不同的醛进行烷基化，以及随后的Saucy-Marbet转移乙烯基化-克莱森重排与分子内Diels-Alder反应的多米诺反应，发现了一个新的二烯酮麝香家族，和总结路易斯酸催化的双键异构化。新合成的二烯酮结构具有令人愉悦的麝香气味，呈现出脂肪、略带果味和绿色的气息。尽管基于 QM/MM 计算，在计算机模拟中预测二烯酮麝香会与 OR5AN1 受体结合，但在体外试验中发现它们是无活性的。后一个结果表明 OR5AN1 受体不是主要的麝香受体，而是主要负责某些大环酮和硝基麝香的动物特性。
更新日期：2020-03-24
中文翻译：
新的刚性二烯酮麝香家族挑战人类嗅觉受体 OR5AN1 的感知范围
通过用but-3-en-1-yn-1-yllithium对不同的醛进行烷基化，以及随后的Saucy-Marbet转移乙烯基化-克莱森重排与分子内Diels-Alder反应的多米诺反应，发现了一个新的二烯酮麝香家族，和总结路易斯酸催化的双键异构化。新合成的二烯酮结构具有令人愉悦的麝香气味，呈现出脂肪、略带果味和绿色的气息。尽管基于 QM/MM 计算，在计算机模拟中预测二烯酮麝香会与 OR5AN1 受体结合，但在体外试验中发现它们是无活性的。后一个结果表明 OR5AN1 受体不是主要的麝香受体，而是主要负责某些大环酮和硝基麝香的动物特性。
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