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Biosynthetic Baeyer-Villiger Chemistry Enables Access to Two Anthracene Scaffolds from a Single Gene Cluster in Deep-Sea-Derived Streptomyces olivaceus SCSIO T05
Zhang, Chunyan1; Sun, Changli; Huang, Hongbo; Gui, Chun1; Wang, Liyan2; Li, Qinglian; Ju, Jianhua1
2018
Source PublicationJOURNAL OF NATURAL PRODUCTS
ISSN0163-3864
Volume81Issue:7Pages:1570
AbstractFour known compounds, rishirilide B (1), rishirilide C (2), lupinacidin A (3), and galvaquinone B (4), representing two anthracene scaffolds typical of aromatic polyketides, were isolated from a culture of the deep-sea derived Streptomyces olivaceus SCSIO T05. From the S. olivaceus producer was cloned and sequenced the rsd biosynthetic gene cluster (BGC) that drives rishirilide biosynthesis. The structural gene rsdK(2) inactivation and heterologous expression of the rsd BGC confirmed the single rsd BGC encodes construction of 1-4 and, thus, accounts for two anthracene scaffolds. Precursor incubation experiments with C-13-labeled acetate revealed that a Baeyer-Villiger-type rearrangement plays a central role in construction of 1-4. Two luciferase monooxygenase components, along with a reductase component, are presumably involved in the Baeyer-Villiger-type rearrangement reaction enabling access to the two anthracene scaffold variants. Engineering of the rsd BGC unveiled three SARP family transcriptional regulators, enhancing anthracene production. Inactivation of rsdR(4), a MarR family transcriptional regulator, failed to impact production of 1-4, although production of 3 was slightly improved; most importantly rsdR(4) inactivation led to the new adduct 6 in high titer. Notably, inactivation of rsdH, a putative amidohydrolase, substantially improved the overall titers of 1-4 by more than 4-fold.
DepartmentLMB
Document Type期刊论文
Identifierhttp://ir.scsio.ac.cn/handle/344004/17656
Collection中科院海洋生物资源可持续利用重点实验室
Affiliation1.Chinese Acad Sci, South China Sea Inst Oceanol, CAS Key Lab Trop Marine Bioresources & Ecol, Guangdong Key Lab Marine Mat Med,RNAM Ctr Marine, 164 West Xingang Rd, Guangzhou 510301, Guangdong, Peoples R China
2.Univ Chinese Acad Sci, 19 Yuquan Rd, Beijing 100049, Peoples R China
3.Shenzhen Univ, Coll Life Sci & Oceanol, Shenzhen Key Lab Marine Bioresource & Ecoenvironm, 3688 Nanhai Ave, Shenzhen 518060, Peoples R China
Recommended Citation
GB/T 7714
Zhang, Chunyan,Sun, Changli,Huang, Hongbo,et al. Biosynthetic Baeyer-Villiger Chemistry Enables Access to Two Anthracene Scaffolds from a Single Gene Cluster in Deep-Sea-Derived Streptomyces olivaceus SCSIO T05[J]. JOURNAL OF NATURAL PRODUCTS,2018,81(7):1570, 1577.
APA Zhang, Chunyan.,Sun, Changli.,Huang, Hongbo.,Gui, Chun.,Wang, Liyan.,...&Ju, Jianhua.(2018).Biosynthetic Baeyer-Villiger Chemistry Enables Access to Two Anthracene Scaffolds from a Single Gene Cluster in Deep-Sea-Derived Streptomyces olivaceus SCSIO T05.JOURNAL OF NATURAL PRODUCTS,81(7),1570.
MLA Zhang, Chunyan,et al."Biosynthetic Baeyer-Villiger Chemistry Enables Access to Two Anthracene Scaffolds from a Single Gene Cluster in Deep-Sea-Derived Streptomyces olivaceus SCSIO T05".JOURNAL OF NATURAL PRODUCTS 81.7(2018):1570.
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