Mechanistic Insights into Polycycle Formation by Reductive Cyclization in Ikarugamycin Biosynthesis
Zhang, GT; Zhang, WJ; Zhang, QB; Shi, T; Ma, L; Zhu, YG; Li, SM; Zhang, HB; Zhao, YL; Shi, R; Zhang, CS; czhang2006@gmail.com
2014
发表期刊ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN1433-7851
卷号53期号:19页码:4840-4844
摘要Ikarugamycin is a member of the polycyclic tetramate macrolactams (PTMs) family of natural products with diverse biological activities. The biochemical mechanisms for the formation of polycyclic ring systems in PTMs remain elusive. The enzymatic mechanism of constructing an inner five-membered ring in ikarugamycin is reported. A three-gene-cassette ikaABC from the marine-derived Streptomyces sp. ZJ306 is sufficient for conferring ikarugamycin production in a heterologous host. IkaC catalyzes a reductive cyclization reaction to form the inner five-membered ring by a Michael addition-like reaction. This study provides the first biochemical evidence for polycycle formation in PTMs and suggests a reductive cyclization strategy which may be potentially applicable in general to the corresponding ring formation in other PTMs.
部门归属[Zhang, Guangtao ; Zhang, Wenjun ; Zhang, Qingbo ; Ma, Liang ; Zhu, Yiguang ; Li, Sumei ; Zhang, Haibo ; Zhang, Changsheng] Chinese Acad Sci, Key Lab Trop Marine Bioresources & Ecol, Guangdong Key Lab Marine Mat Med, RNAM Ctr Marine Microbiol,South China Sea Inst Oc, Guangzhou 510301, Guangdong, Peoples R China ; [Shi, Ting ; Zhao, Yi-Lei] Shanghai Jiao Tong Univ, State Key Lab Microbial Metab, Shanghai 200240, Peoples R China ; [Shi, Ting ; Zhao, Yi-Lei] Shanghai Jiao Tong Univ, Sch Life Sci & Biotechnol, Shanghai 200240, Peoples R China ; [Shi, Rong] Univ Laval, PROTEO, Dept Biochim Microbiol & Bioinformat, Quebec City, PQ G1V 0A6, Canada ; [Shi, Rong] Univ Laval, IBIS, Quebec City, PQ G1V 0A6, Canada
关键词Biosynthesis Heterologous Expression Ikarugamycin Polycyclic Tetramate Macrolactams Reductive Cyclization
学科领域Chemistry
资助者National Natural Science Foundation of China [31125001, 21377085]; Ministry of Science and Technology of China [2010CB833805, 2012AA092104]; Chinese Academy of Sciences [XDA11030403]; Administration of Ocean and Fisheries of Guangdong Province [GD2012-D01-001, GD2012-D01-002] ; National Natural Science Foundation of China [31125001, 21377085]; Ministry of Science and Technology of China [2010CB833805, 2012AA092104]; Chinese Academy of Sciences [XDA11030403]; Administration of Ocean and Fisheries of Guangdong Province [GD2012-D01-001, GD2012-D01-002] ; National Natural Science Foundation of China [31125001, 21377085]; Ministry of Science and Technology of China [2010CB833805, 2012AA092104]; Chinese Academy of Sciences [XDA11030403]; Administration of Ocean and Fisheries of Guangdong Province [GD2012-D01-001, GD2012-D01-002] ; National Natural Science Foundation of China [31125001, 21377085]; Ministry of Science and Technology of China [2010CB833805, 2012AA092104]; Chinese Academy of Sciences [XDA11030403]; Administration of Ocean and Fisheries of Guangdong Province [GD2012-D01-001, GD2012-D01-002]
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收录类别sci
资助项目LMB
资助者National Natural Science Foundation of China [31125001, 21377085]; Ministry of Science and Technology of China [2010CB833805, 2012AA092104]; Chinese Academy of Sciences [XDA11030403]; Administration of Ocean and Fisheries of Guangdong Province [GD2012-D01-001, GD2012-D01-002] ; National Natural Science Foundation of China [31125001, 21377085]; Ministry of Science and Technology of China [2010CB833805, 2012AA092104]; Chinese Academy of Sciences [XDA11030403]; Administration of Ocean and Fisheries of Guangdong Province [GD2012-D01-001, GD2012-D01-002] ; National Natural Science Foundation of China [31125001, 21377085]; Ministry of Science and Technology of China [2010CB833805, 2012AA092104]; Chinese Academy of Sciences [XDA11030403]; Administration of Ocean and Fisheries of Guangdong Province [GD2012-D01-001, GD2012-D01-002] ; National Natural Science Foundation of China [31125001, 21377085]; Ministry of Science and Technology of China [2010CB833805, 2012AA092104]; Chinese Academy of Sciences [XDA11030403]; Administration of Ocean and Fisheries of Guangdong Province [GD2012-D01-001, GD2012-D01-002]
WOS记录号WOS:000335202700013
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被引频次:31[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.scsio.ac.cn/handle/344004/10440
专题中科院海洋生物资源可持续利用重点实验室
通讯作者czhang2006@gmail.com
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Zhang, GT,Zhang, WJ,Zhang, QB,et al. Mechanistic Insights into Polycycle Formation by Reductive Cyclization in Ikarugamycin Biosynthesis[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2014,53(19):4840-4844.
APA Zhang, GT.,Zhang, WJ.,Zhang, QB.,Shi, T.,Ma, L.,...&czhang2006@gmail.com.(2014).Mechanistic Insights into Polycycle Formation by Reductive Cyclization in Ikarugamycin Biosynthesis.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,53(19),4840-4844.
MLA Zhang, GT,et al."Mechanistic Insights into Polycycle Formation by Reductive Cyclization in Ikarugamycin Biosynthesis".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 53.19(2014):4840-4844.
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