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Characterization of the flavoenzyme XiaK as an N-hydroxylase and implications in indolosesquiterpene diversification

文献类型：期刊论文

作者Zhang, Qingbo1; Li, Huixian1,2; Yu, Lu3,4; Sun, Yu5; Zhu, Yiguang1; Zhu, Hanning1; Zhang, Liping1; Li, Shu-Ming6; Shen, Yuemao7; Tian, Changlin3
刊名CHEMICAL SCIENCE
出版日期2017-07-01
卷号8期号:7页码:5067-5077
DOI10.1039/c7sc01182b
文献子类Article
英文摘要Flavoenzymes are ubiquitous in biological systems and catalyze a diverse range of chemical transformations. The flavoenzyme XiaK from the biosynthetic pathway of the indolosesquiterpene xiamycin A is demonstrated to mediate the in vivo biotransformation of xiamycin A into multiple products, including a chlorinated adduct as well as dimers characterized by C-N and N-N linkages that are hypothesized to form via radical-based mechanisms. Isolation and characterization of XiaK in vitro shows that it acts as a flavin-dependent N-hydroxylase that catalyzes the hydroxylation of xiamycin A at the carbazole nitrogen to form N-hydroxyxiamycin, a product which was overlooked in earlier in vivo experiments because its chemical and chromatographic properties are similar to those of oxiamycin. N-Hydroxyxiamycin is shown to be unstable under aerobic conditions, and characterization by electron paramagnetic resonance spectroscopy demonstrates formation of an N-hydroxycarbazole radical adduct. This radical species is proposed to serve as a key intermediate leading to the formation of the multiple xiamycin A adducts. This study suggests that non-enzyme catalyzed reactions may play a greater role in the biosynthesis of natural products than has been previously recognized.
WOS关键词GENE-CLUSTER REVEALS ; NATURAL-PRODUCTS ; BIOSYNTHETIC-PATHWAY ; BACTERIAL SYNTHESIS ; CRYSTAL-STRUCTURE ; CYTOCHROME-P450 ; STREPTOMYCES ; MONOOXYGENASE ; INSIGHTS ; XIAMYCIN
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000404617300043
资助机构Chinese Academy of Sciences(XDA11030403 ; Chinese Academy of Sciences(XDA11030403 ; Chinese Academy of Sciences(XDA11030403 ; Chinese Academy of Sciences(XDA11030403 ; National Natural Science Foundation of China(41406183 ; National Natural Science Foundation of China(41406183 ; National Natural Science Foundation of China(41406183 ; National Natural Science Foundation of China(41406183 ; Administration of Ocean and Fisheries of Guangdong Province(GD2012-D01-002) ; Administration of Ocean and Fisheries of Guangdong Province(GD2012-D01-002) ; Administration of Ocean and Fisheries of Guangdong Province(GD2012-D01-002) ; Administration of Ocean and Fisheries of Guangdong Province(GD2012-D01-002) ; China Scholarship Council (CSC) ; China Scholarship Council (CSC) ; China Scholarship Council (CSC) ; China Scholarship Council (CSC) ; Deutscher Akademischer Austausch Dienst (DAAD) ; Deutscher Akademischer Austausch Dienst (DAAD) ; Deutscher Akademischer Austausch Dienst (DAAD) ; Deutscher Akademischer Austausch Dienst (DAAD) ; Science and Technology Program of Guangzhou ; Science and Technology Program of Guangzhou ; Science and Technology Program of Guangzhou ; Science and Technology Program of Guangzhou ; K. C. Wong Education Foundation, Hong Kong ; K. C. Wong Education Foundation, Hong Kong ; K. C. Wong Education Foundation, Hong Kong ; K. C. Wong Education Foundation, Hong Kong ; National Institutes of Health(GM040541) ; National Institutes of Health(GM040541) ; National Institutes of Health(GM040541) ; National Institutes of Health(GM040541) ; Welch Foundation(F-1511) ; Welch Foundation(F-1511) ; Welch Foundation(F-1511) ; Welch Foundation(F-1511) ; QYZDJ-SSW-DQC004) ; QYZDJ-SSW-DQC004) ; QYZDJ-SSW-DQC004) ; QYZDJ-SSW-DQC004) ; 31300084 ; 31300084 ; 31300084 ; 31300084 ; 31630004 ; 31630004 ; 31630004 ; 31630004 ; 31290233 ; 31290233 ; 31290233 ; 31290233 ; 31125001) ; 31125001) ; 31125001) ; 31125001) ; Chinese Academy of Sciences(XDA11030403 ; Chinese Academy of Sciences(XDA11030403 ; Chinese Academy of Sciences(XDA11030403 ; Chinese Academy of Sciences(XDA11030403 ; National Natural Science Foundation of China(41406183 ; National Natural Science Foundation of China(41406183 ; National Natural Science Foundation of China(41406183 ; National Natural Science Foundation of China(41406183 ; Administration of Ocean and Fisheries of Guangdong Province(GD2012-D01-002) ; Administration of Ocean and Fisheries of Guangdong Province(GD2012-D01-002) ; Administration of Ocean and Fisheries of Guangdong Province(GD2012-D01-002) ; Administration of Ocean and Fisheries of Guangdong Province(GD2012-D01-002) ; China Scholarship Council (CSC) ; China Scholarship Council (CSC) ; China Scholarship Council (CSC) ; China Scholarship Council (CSC) ; Deutscher Akademischer Austausch Dienst (DAAD) ; Deutscher Akademischer Austausch Dienst (DAAD) ; Deutscher Akademischer Austausch Dienst (DAAD) ; Deutscher Akademischer Austausch Dienst (DAAD) ; Science and Technology Program of Guangzhou ; Science and Technology Program of Guangzhou ; Science and Technology Program of Guangzhou ; Science and Technology Program of Guangzhou ; K. C. Wong Education Foundation, Hong Kong ; K. C. Wong Education Foundation, Hong Kong ; K. C. Wong Education Foundation, Hong Kong ; K. C. Wong Education Foundation, Hong Kong ; National Institutes of Health(GM040541) ; National Institutes of Health(GM040541) ; National Institutes of Health(GM040541) ; National Institutes of Health(GM040541) ; Welch Foundation(F-1511) ; Welch Foundation(F-1511) ; Welch Foundation(F-1511) ; Welch Foundation(F-1511) ; QYZDJ-SSW-DQC004) ; QYZDJ-SSW-DQC004) ; QYZDJ-SSW-DQC004) ; QYZDJ-SSW-DQC004) ; 31300084 ; 31300084 ; 31300084 ; 31300084 ; 31630004 ; 31630004 ; 31630004 ; 31630004 ; 31290233 ; 31290233 ; 31290233 ; 31290233 ; 31125001) ; 31125001) ; 31125001) ; 31125001)
源URL[http://ir.hfcas.ac.cn:8080/handle/334002/32015]  
专题合肥物质科学研究院_中科院强磁场科学中心
作者单位1.Chinese Acad Sci, CAS Key Lab Trop Marine Bioresources & Ecol, Guangdong Key Lab Marine Mat Med, South China Sea Inst Oceanol, 164 West Xingang Rd, Guangzhou 510301, Guangdong, Peoples R China
2.Sun Yat Sen Univ, South China Sea Resource Exploitat & Protect Coll, Sch Marine Sci, Inst Marine Nat Prod, 135 West Xingang Rd, Guangzhou 510006, Guangdong, Peoples R China
3.Univ Sci & Technol China, Sch Life Sci, Hefei Natl Lab Microscale Phys Sci, Hefei 230027, Peoples R China
4.Chinese Acad Sci, High Magnet Field Lab, Hefei 230031, Peoples R China
5.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
6.Philipps Univ Marburg, Inst Pharmazeut Biol & Biotechnol, Deutschhausstr 17a, D-35037 Marburg, Germany
7.Shandong Univ, Sch Life Sci, State Key Lab Microbial Technol, Jinan 250100, Peoples R China
8.Univ Texas Austin, Dept Chem, Coll Pharm, Div Chem Biol & Med Chem, Austin, TX 78712 USA
推荐引用方式
GB/T 7714		 Zhang, Qingbo,Li, Huixian,Yu, Lu,et al. Characterization of the flavoenzyme XiaK as an N-hydroxylase and implications in indolosesquiterpene diversification[J]. CHEMICAL SCIENCE,2017,8(7):5067-5077.
APA Zhang, Qingbo.,Li, Huixian.,Yu, Lu.,Sun, Yu.,Zhu, Yiguang.,...&Zhang, Changsheng.(2017).Characterization of the flavoenzyme XiaK as an N-hydroxylase and implications in indolosesquiterpene diversification.CHEMICAL SCIENCE,8(7),5067-5077.
MLA Zhang, Qingbo,et al."Characterization of the flavoenzyme XiaK as an N-hydroxylase and implications in indolosesquiterpene diversification".CHEMICAL SCIENCE 8.7(2017):5067-5077.

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来源：合肥物质科学研究院

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