| Tropane alkaloids biosynthesis involves an unusual type III polyketide synthase and non-enzymatic condensation | |
Huang, Jian-Ping1,2; Fang, Chengli3,4; Ma, Xiaoyan1,2,5; Wang, Li1,2 ; Yang, Jing1,2; Luo, Jianying1,2; Yan, Yijun1,2; Zhang, Yu3,4; Huang, Sheng-Xiong1,2
| |
| Corresponding Author | Zhang, Yu(yzhang@sippe.ac.cn) ; Huang, Sheng-Xiong(sxhuang@mail.kib.ac.cn) |
| 2019-09-06 | |
| Source Publication | NATURE COMMUNICATIONS
 |
| ISSN | 2041-1723 |
| Volume | 10Pages:8 |
| Abstract | The skeleton of tropane alkaloids is derived from ornithine-derived N-methylpyrrolinium and two malonyl-CoA units. The enzymatic mechanism that connects N-methylpyrrolinium and malonyl-CoA units remains unknown. Here, we report the characterization of three pyrrolidine ketide synthases (PYKS), AaPYKS, DsPYKS, and AbPYKS, from three different hyoscyamine- and scopolamine- producing plants. By examining the crystal structure and biochemical activity of AaPYKS, we show that the reaction mechanism involves PYKS-mediated malonyl-CoA condensation to generate a 3-oxo-glutaric acid intermediate that can undergo non-enzymatic Mannich-like condensation with N-methylpyrrolinium to yield the racemic 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoic acid. This study therefore provides a long sought-after biosynthetic mechanism to explain condensation between N-methylpyrrolinium and acetate units and, more importantly, identifies an unusual plant type III polyketide synthase that can only catalyze one round of malonyl- CoA condensation. |
| DOI | 10.1038/s41467-019-11987-z |
| Indexed By | SCI |
| Language | 英语 |
| WOS ID | WOS:000484598900003 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.kib.ac.cn/handle/151853/68659 |
| Collection | 植物化学与西部植物资源持续利用国家重点实验室 |
| Corresponding Author | Zhang, Yu; Huang, Sheng-Xiong |
| Affiliation | 1.Chinese Acad Sci, State Key Lab Phytochem & Plant Resources West Ch, Kunming Inst Bot, Kunming 650201, Yunnan, Peoples R China 2.Chinese Acad Sci, CAS Ctr Excellence Mol Plant Sci, Kunming Inst Bot, Kunming 650201, Yunnan, Peoples R China 3.Chinese Acad Sci, Key Lab Synthet Biol, Inst Plant Physiol & Ecol, Shanghai 200032, Peoples R China 4.Chinese Acad Sci, CAS Ctr Excellence Mol Plant Sci, Inst Plant Physiol & Ecol, Shanghai 200032, Peoples R China 5.Sichuan Univ Sci & Engn, Sch Chem & Chem Engn, Zigong 643000, Peoples R China |
| Recommended Citation GB/T 7714 | Huang, Jian-Ping,Fang, Chengli,Ma, Xiaoyan,et al. Tropane alkaloids biosynthesis involves an unusual type III polyketide synthase and non-enzymatic condensation[J]. NATURE COMMUNICATIONS,2019,10:8. |
| APA | Huang, Jian-Ping.,Fang, Chengli.,Ma, Xiaoyan.,Wang, Li.,Yang, Jing.,...&Huang, Sheng-Xiong.(2019).Tropane alkaloids biosynthesis involves an unusual type III polyketide synthase and non-enzymatic condensation.NATURE COMMUNICATIONS,10,8. |
| MLA | Huang, Jian-Ping,et al."Tropane alkaloids biosynthesis involves an unusual type III polyketide synthase and non-enzymatic condensation".NATURE COMMUNICATIONS 10(2019):8. |
| Files in This Item: | ||||||
| File Name/Size | DocType | Version | Access | License | ||
| Huang-2019-Tropane a（1048KB） | 期刊论文 | 出版稿 | 开放获取 | CC BY-NC-SA | View Download | |
Items in the repository are protected by copyright, with all rights reserved, unless otherwise indicated.
Edit Comment