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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

Organic & biomolecular chemistry, 2021-08, Vol.19 (3), p.665-6656 [Periódico revisado por pares]

England: Royal Society of Chemistry

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Título:
1,10/1,11-Cyclization catalyzed by diverged plant sesquiterpene synthases is dependent on a single residue
Autor: Huang, Jin-Quan ; Li, Dong-Mei ; Li, Jian-Xu ; Lin, Jia-Ling ; Tian, Xiu ; Wang, Ling-Jian ; Chen, Xiao-Ya ; Fang, Xin
Assuntos: Alkyl and Aryl Transferases - chemistry ; Alkyl and Aryl Transferases - genetics ; Alkyl and Aryl Transferases - metabolism ; Aristolochene synthase ; Biocatalysis ; Catalytic Domain ; Cyclization ; Germacrene ; Herbal medicine ; Models, Molecular ; Mutagenesis ; Mutagenesis, Site-Directed ; Mutation ; Nicotiana - enzymology ; Patchoulol ; Phylogeny ; Plant species ; Residues ; Severe acute respiratory syndrome coronavirus 2 ; Site-directed mutagenesis ; Terpene synthase ; Terpenes ; Traditional Chinese medicine
É parte de: Organic & biomolecular chemistry, 2021-08, Vol.19 (3), p.665-6656
Notas: Electronic supplementary information (ESI) available. See DOI
10.1039/d1ob00827g
Descrição: 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 pre NSE/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 pre NSE/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. A conserved amino acid residue responsible for the 1,10- or 1,11-cyclization of FDP was identified in sesquiterpene synthases of different sources and functions, shedding new light on the mechanisms of sesquiterpene cyclization.
Editor: England: Royal Society of Chemistry
Idioma: Inglês

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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

England: Royal Society of Chemistry

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