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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.
  • Huang JQ; Yunnan University, Kunming, PR China and National Key Laboratory of Plant Molecular Genetics, Institute of Plant Physiology and Ecology/CAS Center for Excellence in Molecular Plant Sciences, Chinese Academy of Sciences, Shanghai, PR China.
  • Li DM; Yunnan University, Kunming, PR China and State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, PR China. xinfang@mail.kib.ac.cn.
  • Li JX; National Key Laboratory of Plant Molecular Genetics, Institute of Plant Physiology and Ecology/CAS Center for Excellence in Molecular Plant Sciences, Chinese Academy of Sciences, Shanghai, PR China.
  • Lin JL; National Key Laboratory of Plant Molecular Genetics, Institute of Plant Physiology and Ecology/CAS Center for Excellence in Molecular Plant Sciences, Chinese Academy of Sciences, Shanghai, PR China and School of Life Science and Technology, ShanghaiTech University, Shanghai, PR China.
  • Tian X; National Key Laboratory of Plant Molecular Genetics, Institute of Plant Physiology and Ecology/CAS Center for Excellence in Molecular Plant Sciences, Chinese Academy of Sciences, Shanghai, PR China.
  • Wang LJ; National Key Laboratory of Plant Molecular Genetics, Institute of Plant Physiology and Ecology/CAS Center for Excellence in Molecular Plant Sciences, Chinese Academy of Sciences, Shanghai, PR China.
  • Chen XY; National Key Laboratory of Plant Molecular Genetics, Institute of Plant Physiology and Ecology/CAS Center for Excellence in Molecular Plant Sciences, Chinese Academy of Sciences, Shanghai, PR China.
  • Fang X; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, PR China. xinfang@mail.kib.ac.cn.
Org Biomol Chem ; 19(30): 6650-6656, 2021 08 05.
Article in English | MEDLINE | ID: covidwho-1343477
ABSTRACT
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 preNSE/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 preNSE/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.
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Full text: Available Collection: International databases Database: MEDLINE Main subject: Alkyl and Aryl Transferases / Biocatalysis Type of study: Randomized controlled trials Language: English Journal: Org Biomol Chem Journal subject: Biochemistry / Chemistry Year: 2021 Document Type: Article

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Full text: Available Collection: International databases Database: MEDLINE Main subject: Alkyl and Aryl Transferases / Biocatalysis Type of study: Randomized controlled trials Language: English Journal: Org Biomol Chem Journal subject: Biochemistry / Chemistry Year: 2021 Document Type: Article