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1,10/1,11-Cyclization catalyzed by diverged plant sesquiterpene synthases is dependent on a single residue
Huang,Jin-Quan; Li,Dong-Mei; Li,Jian-Xu; Lin,Jia-Ling; Tian,Xiu; Wang,Ling-Jian; Chen,Xiao-Ya; Fang,Xin
2021
发表期刊ORGANIC & BIOMOLECULAR CHEMISTRY
ISSN1477-0520
卷号19期号:30页码:6650-6656
摘要The exquisite chemodiversity of terpenoids is the product of the large diverse terpene synthase (TPS) superfamily. Here, by using structural and phylogenetic analyses and site-directed mutagenesis, we identified a residue (Cys440 in Nicotiana tabacum 5-epi-aristolochene synthase) proximal to an ion-binding motif common to all TPSs and named the (NSE)-N-pre/DTE residue, which determines the product specificity of sesquiterpene synthases from different plant species. In sesquiterpene synthases catalyzing 1,10-cyclization (1,10-cyclases) of farnesyl diphosphate, mutation of the residue in both specific and promiscuous 1,10-cyclases from different lineages leads to the accumulation of monocyclic germacrene A-11-ol, which is short-circuited from complex cyclization cascades, suggesting a key role of this residue in generating the first common intermediate of 1,10-cyclization. Altering this residue in a specific 1,11-cyclase results in alternative 1,10-cyclization products. Moreover, the (NSE)-N-pre/DTE residue can be harnessed to engineer highly specific sesquiterpene synthases for an improved proportion of high-value terpenoids, such as patchoulol, a main constituent of several traditional Chinese medicines that could treat SARS-CoV-2.
关键词ACTIVE-SITE RESIDUES ARISTOLOCHENE SYNTHASE ARTEMISIA-ANNUA BIOLOGY IDENTIFICATION BIOSYNTHESIS EXPRESSION CLONING GENES
DOI10.1039/d1ob00827g
WOS记录号WOS:000673751500001
引用统计
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/73697
专题中国科学院昆明植物研究所
作者单位1.[Huang, Jin-Quan
2.Yunnan Univ, Kunming, Yunnan, Peoples R China
3.Li, Jian-Xu
4.Lin, Jia-Ling
5.Tian, Xiu
6.Wang, Ling-Jian
7.Chinese Acad Sci, CAS Ctr Excellence Mol Plant Sci, Inst Plant Physiol & Ecol, Natl Key Lab Plant Mol Genet, Shanghai, Peoples R China
8.[Li, Dong-Mei
9.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming, Yunnan, Peoples R China
10.ShanghaiTech Univ, Sch Life Sci & Technol, Shanghai, Peoples R China
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GB/T 7714
Huang,Jin-Quan,Li,Dong-Mei,Li,Jian-Xu,et al. 1,10/1,11-Cyclization catalyzed by diverged plant sesquiterpene synthases is dependent on a single residue[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2021,19(30):6650-6656.
APA Huang,Jin-Quan.,Li,Dong-Mei.,Li,Jian-Xu.,Lin,Jia-Ling.,Tian,Xiu.,...&Fang,Xin.(2021).1,10/1,11-Cyclization catalyzed by diverged plant sesquiterpene synthases is dependent on a single residue.ORGANIC & BIOMOLECULAR CHEMISTRY,19(30),6650-6656.
MLA Huang,Jin-Quan,et al."1,10/1,11-Cyclization catalyzed by diverged plant sesquiterpene synthases is dependent on a single residue".ORGANIC & BIOMOLECULAR CHEMISTRY 19.30(2021):6650-6656.
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