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Design and Biosynthesis of Dimeric Alboflavusins with Biaryl Linkages via Regiospecific C-C Bond Coupling
Guo, Zhengyan; Li, Pengwei; Chen, Guozhu1; Li, Chao2; Cao, Zhenju2; Zhang, Yuwei2; Ren, Jinwei3; Xiang, Hua2; Lin, Shuangjun4; Ju, Jianhua5; Chen, Yihua2
2018
Source PublicationJOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN0002-7863
Volume140Issue:51Pages:18009
AbstractAlboflavusins (AFNs) are a group of cyclo-hexapeptides with moderate antibacterial and antitumor activities from Streptomyces alboflavus sp. 313. In vivo and in vitro studies proposed that AFNs are biosynthesized by a nonribosomal peptide synthetase machinery, and the 6-Cl-L-Trp precursor is supplied by a tryptophan halogenase gene located outside the afn gene cluster. Guided by the structure-activity relationship knowledge about the AFN-like cyclo-hexapeptides, two dimeric AFNs (di-AFNs) with regiospecific biaryl linkages were designed and generated biotechnologically by expressing the P450 gene hmtS or clpS in S. alboflavus wild-type and mutant strains. The di-AFNs displayed much better antibacterial and antitumor activities than their monomers as anticipated, exemplifying a rational strategy to generate natural product congeners with improved bioactivities.
DepartmentLMB
DOI10.1021/jacs.8b10136
Citation statistics
Document Type期刊论文
Identifierhttp://ir.scsio.ac.cn/handle/344004/17930
Collection中科院海洋生物资源可持续利用重点实验室
Affiliation1.Chinese Acad Sci, State Key Lab Microbial Resources, Inst Microbiol, Beijing 100101, Peoples R China
2.Acad Mil Med Sci, Inst Mil Cognit & Brain Sci, Beijing 100850, Peoples R China
3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
4.Chinese Acad Sci, State Key Lab Mycol, Inst Microbiol, Beijing 100101, Peoples R China
5.Shanghai Jiao Tong Univ, State Key Lab Microbial Metab, Sch Life Sci & Biotechnol, Shanghai 200030, Peoples R China
6.Chinese Acad Sci, CAS Key Lab Trop Marine Bioresources & Ecol, South China Sea Inst Oceanol, Guangzhou 510301, Guangdong, Peoples R China
Recommended Citation
GB/T 7714
Guo, Zhengyan,Li, Pengwei,Chen, Guozhu,et al. Design and Biosynthesis of Dimeric Alboflavusins with Biaryl Linkages via Regiospecific C-C Bond Coupling[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2018,140(51):18009, 18015.
APA Guo, Zhengyan.,Li, Pengwei.,Chen, Guozhu.,Li, Chao.,Cao, Zhenju.,...&Chen, Yihua.(2018).Design and Biosynthesis of Dimeric Alboflavusins with Biaryl Linkages via Regiospecific C-C Bond Coupling.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,140(51),18009.
MLA Guo, Zhengyan,et al."Design and Biosynthesis of Dimeric Alboflavusins with Biaryl Linkages via Regiospecific C-C Bond Coupling".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 140.51(2018):18009.
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