Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids
文献类型：期刊论文
| 作者 | Yan, Yijun1; Yang, Jing1 ; Yu, Zhiyin1; Yu, Mingming1; Ma, Ya-Tuan1; Wang, Li1; Su, Can1; Luo, Jianying1; Horsman, Geoffrey P.2; Huang, Sheng-Xiong1
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| 刊名 | NATURE COMMUNICATIONS
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| 出版日期 | 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 |
| 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. |
入库方式： OAI收割
来源：昆明植物研究所
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