Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids
Yan, Yijun1; Yang, Jing1; Yu, Zhiyin1; Yu, Mingming1; Ma, Ya-Tuan1; Wang, Li1; Su, Can1; Luo, Jianying1; Horsman, Geoffrey P.2; Huang, Sheng-Xiong1
2016-10-07
Source PublicationNATURE COMMUNICATIONS
Volume7Issue:1Pages:1
AbstractThe pyridine ring is a potent pharmacophore in alkaloid natural products. Nonetheless, its biosynthetic pathways are poorly understood. Rubrolones A and B are tropolone alkaloid natural products possessing a unique tetra-substituted pyridine moiety. Here, we report the gene cluster and propose a biosynthetic pathway for rubrolones, identifying a key intermediate that accumulates upon inactivation of sugar biosynthetic genes. Critically, this intermediate was converted to the aglycones of rubrolones by non-enzymatic condensation and cyclization with either ammonia or anthranilic acid to generate the respective pyridine rings. We propose that this non-enzymatic reaction occurs via hydrolysis of the key intermediate, which possesses a 1,5-dione moiety as an amine acceptor capable of cyclization. This study suggests that 1,5-dione moieties may represent a general strategy for pyridine ring biosynthesis, and more broadly highlights the utility of non-enzymatic diversification for exploring and expanding natural product chemical space.
DOI10.1038/ncomms13083
Indexed BySCI
Language英语
WOS Research AreaScience & Technology - Other Topics
WOS SubjectMultidisciplinary Sciences
WOS IDWOS:000385588000001
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Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/33643
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China
2.Wilfrid Laurier Univ, Dept Chem & Biochem, Waterloo, ON N2L 3C5, Canada
Recommended Citation
GB/T 7714
Yan, Yijun,Yang, Jing,Yu, Zhiyin,et al. Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids[J]. NATURE COMMUNICATIONS,2016,7(1):1.
APA Yan, Yijun.,Yang, Jing.,Yu, Zhiyin.,Yu, Mingming.,Ma, Ya-Tuan.,...&Huang, Sheng-Xiong.(2016).Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids.NATURE COMMUNICATIONS,7(1),1.
MLA Yan, Yijun,et al."Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids".NATURE COMMUNICATIONS 7.1(2016):1.
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