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Identification of key amino acid residues determining product specificity of 2,3-oxidosqualene cyclase in Oryza species

文献类型： 外文期刊

作者： Xue, Zheyong 1 ; Tan, Zhengwei 1 ; Huang, Ancheng 2 ; Zhou, Yuan 1 ; Sun, Juncong 1 ; Wang, Xiaoning 5 ; Thimmappa, Ra 1 ;

作者机构： 1.Chinese Acad Sci, Key Lab Plant Mol Physiol, Inst Bot, Beijing 100093, Peoples R China

2.John Innes Ctr, Dept Metab Biol, Norwich Res Pk, Norwich NR4 7UH, Norfolk, England

3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China

4.Henan Acad Agr Sci, Henan Sesame Res Ctr, Zhengzhou 450002, Henan, Peoples R China

5.Shandong Univ, Sch Pharmaceut Sci, Minist Educ, Dept Nat Prod Chem,Key Lab Chem Biol, 44 West Wenhua Rd, Jinan 250012, Shandong, Peoples R China

关键词： chemical diversity; conformation; orysatinol; oxidosqualene cyclase (OSC); parkeol; product specificity; rice; triterpene

期刊名称：NEW PHYTOLOGIST （ 影响因子：10.151； 五年影响因子：10.475 ）

ISSN： 0028-646X

年卷期： 2018 年 218 卷 3 期

页码：

收录情况： SCI

摘要： Triterpene synthases, also known as 2,3-oxidosqualene cyclases (OSCs), synthesize diverse triterpene skeletons that form the basis of an array of functionally divergent steroids and triterpenoids. Tetracyclic and pentacyclic triterpene skeletons are synthesized via protosteryl and dammarenyl cations, respectively. The mechanism of conversion between two scaffolds is not well understood. Here, we report a promiscuous OSC from rice (Oryza sativa) (OsOS) that synthesizes a novel pentacyclic triterpene orysatinol as its main product. The OsOS gene is widely distributed in indica subspecies of cultivated rice and in wild rice accessions. Previously, we have characterized a different OSC, OsPS, a tetracyclic parkeol synthase found in japonica subspecies. Phylogenetic and protein structural analyses identified three key amino acid residues (#732, #365, #124) amongst 46 polymorphic sites that determine functional conversion between OsPS and OsOS, specifically, the chair-semi(chair)-chair and chair-boat-chair interconversions. The different orientation of a fourth amino acid residue Y257 was shown to be important for functional conversion The discovery of orysatinol unlocks a new path to triterpene diversity in nature. Our findings also reveal mechanistic insights into the cyclization of oxidosqualene into tetra- and pentacyclic skeletons, and provide a new strategy to identify key residues determining OSC specificity.

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