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 AuthorZhang, Yu(yzhang@sippe.ac.cn) ; Huang, Sheng-Xiong(sxhuang@mail.kib.ac.cn)
2019-09-06
Source PublicationNATURE COMMUNICATIONS
ISSN2041-1723
Volume10Pages:8
AbstractThe 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.
DOI10.1038/s41467-019-11987-z
Indexed BySCI
Language英语
WOS IDWOS:000484598900003
Citation statistics
Document Type期刊论文
Identifierhttp://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 AuthorZhang, Yu; Huang, Sheng-Xiong
Affiliation1.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.
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