化学
黄素组
吲哚试验
戒指(化学)
催化作用
氧气
氧化磷酸化
溶剂
立体化学
药物化学
有机化学
生物化学
酶
作者
Yu Dai,Xiulan Xie,Hao-Fu Dai,Shu-Ming Li
出处
期刊:PubMed
日期:2023-06-09
卷期号:25 (22): 4092-4097
标识
DOI:10.1021/acs.orglett.3c01320
摘要
Most naturally occurring indole diterpenes share a 6/5/5/6/6/6 hexacyclic ring system, while a 6/8/6/6/6 pentacyclic skeleton is occasionally observed. In this study, we demonstrate the formation of an eight-membered C-N heteroring via nonenzymatic flavin-catalyzed oxidative indole ring opening. More interestingly, 18O-labeled experiments proved that the two incorporated oxygen atoms are predominantly originated from water instead of molecular oxygen. In this process, the oxidized form of flavin catalyzes two successive oxidations of amines to imines with involvement of hydrolysis for the ring expansion. The reduced flavin is then regenerated by oxidation with molecular oxygen to form H2O2.
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