Side Products of Recombinant Amorpha-4,11-diene Synthase and Their Effect on Microbial Artemisinin Production

doi:10.1021/acs.jafc.0c07462

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	Side Products of Recombinant Amorpha-4,11-diene Synthase and Their Effect on Microbial Artemisinin Production
	Huang,Jin-Quan ; Li,Dong-Mei ; Tian,Xiu ; Lin,Jia-Ling ; Yang,Lei ; Xu,Jing-Jing ; Fang,Xin
	2021
Source Publication	JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
ISSN	0021-8561
Volume	69 Issue:7 Pages:2168-2178
Abstract	Amorpha-4,11-diene synthase (ADS) is the first committed enzyme in the biosynthesis of artemisinin. Artemisinin production by biobased fermentation is considered a reliable alternative pathway. Heterologously expressed ADS has been established to generate several minor products, including structural analogues of amorpha-4,11-diene, but their fate in fermentation is still unknown. Here, using chiral analysis, we found that ADS produces one of the analogues, amorpha-4-en-11-ol, as a pair of epimers. Labeling experiments revealed that ADS mutants yielded amorphene-type sesquiterpenes, indicating the co-occurrence of initial 1,6 and 1,10 cyclization of farnesyl diphosphate in a single enzyme. Interestingly, the immediate downstream oxidase CYP71AV1 had very low affinity to the side products of the recombinant ADS, including amorpha-4-en-7-ol, which is structurally similar to amorpha-4,11-diene. Our data uncover the complex catalytic mechanism of recombinant ADS and reveal a potential negative effect of the side products of recombinant ADS on the production of the artemisinin precursor in microbes.
Keyword	artemisinin chiral analysis cytochrome P450 monooxygenases labeling sesquiterpenes specialized metabolism pathway terpene synthases
DOI	10.1021/acs.jafc.0c07462
WOS ID	WOS:000624326000015
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Document Type	期刊论文
Identifier	http://ir.kib.ac.cn/handle/151853/73698
Collection	中国科学院昆明植物研究所
Affiliation	1.[Huang, Jin-Quan 2.Yunnan Univ, Kunming 650091, Yunnan, Peoples R China 3.Tian, Xiu 4.Chinese Acad Sci, Inst Plant Physiol & Ecol, Natl Key Lab Plant Mol Genet, CAS Ctr Excellence Mol Plant Sci, Shanghai 200032, Peoples R China 5.[Li, Dong-Mei 6.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Yunnan, Peoples R China 7.ShanghaiTech Univ, Sch Life Sci & Technol, Shanghai 200031, Peoples R China 8.[Yang, Lei 9.Shanghai Chenshan Bot Garden, Shanghai Key Lab Plant Funct Genom & Resources, Plant Sci Res Ctr, Shanghai 201602, Peoples R China
Recommended Citation GB/T 7714	Huang,Jin-Quan,Li,Dong-Mei,Tian,Xiu,et al. Side Products of Recombinant Amorpha-4,11-diene Synthase and Their Effect on Microbial Artemisinin Production[J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,2021,69(7):2168-2178.
APA	Huang,Jin-Quan.,Li,Dong-Mei.,Tian,Xiu.,Lin,Jia-Ling.,Yang,Lei.,...&Fang,Xin.(2021).Side Products of Recombinant Amorpha-4,11-diene Synthase and Their Effect on Microbial Artemisinin Production.JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,69(7),2168-2178.
MLA	Huang,Jin-Quan,et al."Side Products of Recombinant Amorpha-4,11-diene Synthase and Their Effect on Microbial Artemisinin Production".JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 69.7(2021):2168-2178.

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