Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids

CORC > 昆明植物研究所 > 中国科学院昆明植物研究所 > 植物化学与西部植物资源持续利用国家重点实验室

	Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids
	Yan, Yijun 1; Yang, Jing1 ; Yu, Zhiyin 1; Yu, Mingming 1; Ma, Ya-Tuan 1; Wang, Li 1; Su, Can 1; Luo, Jianying1 ; Horsman, Geoffrey P.2; Huang, Sheng-Xiong1
刊名	NATURE COMMUNICATIONS
	2016-10-07
卷号	7 期号:1 页码:1
英文摘要	The 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.
类目[WOS]	Multidisciplinary Sciences
研究领域[WOS]	Science & Technology - Other Topics
关键词[WOS]	R1128 POLYKETIDE SYNTHASE ; ECHINORUBER SP-NOV ; NATURAL-PRODUCTS ; HETEROLOGOUS EXPRESSION ; AZEPINE ALKALOIDS ; TROPANE ALKALOIDS ; GENE-CLUSTER ; RED PIGMENT ; STREPTOMYCES ; PYRROLIDINE
收录类别	SCI
语种	英语
WOS记录号	WOS:000385588000001
内容类型	期刊论文
源URL	[http://ir.kib.ac.cn/handle/151853/33643]
专题	昆明植物研究所_植物化学与西部植物资源持续利用国家重点实验室
作者单位	1.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
推荐引用方式 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.