C3′-Deoxygenation of Paromamine Catalyzed by a Radical S -Adenosylmethionine Enzyme: Characterization of the Enzyme AprD4 and Its Reductase Partner AprD3
2016; Wiley; Volume: 128; Issue: 11 Linguagem: Inglês
10.1002/ange.201510635
ISSN1521-3757
AutoresHak Joong Kim, Jake A. LeVieux, Yu-Cheng Yeh, Hung‐wen Liu,
Tópico(s)Metal-Catalyzed Oxygenation Mechanisms
ResumoAngewandte ChemieVolume 128, Issue 11 p. 3788-3792 Zuschrift C3′-Deoxygenation of Paromamine Catalyzed by a Radical S-Adenosylmethionine Enzyme: Characterization of the Enzyme AprD4 and Its Reductase Partner AprD3 Hak Joong Kim, Hak Joong Kim Division of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Texas at Austin, Austin, TX, 78712 USASearch for more papers by this authorJake LeVieux, Jake LeVieux Division of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Texas at Austin, Austin, TX, 78712 USASearch for more papers by this authorYu-Cheng Yeh, Yu-Cheng Yeh Division of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Texas at Austin, Austin, TX, 78712 USASearch for more papers by this authorProf. Dr. Hung-wen Liu, Corresponding Author Prof. Dr. Hung-wen Liu [email protected] orcid.org/0000-0001-8953-4794 Division of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Texas at Austin, Austin, TX, 78712 USASearch for more papers by this author Hak Joong Kim, Hak Joong Kim Division of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Texas at Austin, Austin, TX, 78712 USASearch for more papers by this authorJake LeVieux, Jake LeVieux Division of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Texas at Austin, Austin, TX, 78712 USASearch for more papers by this authorYu-Cheng Yeh, Yu-Cheng Yeh Division of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Texas at Austin, Austin, TX, 78712 USASearch for more papers by this authorProf. Dr. Hung-wen Liu, Corresponding Author Prof. Dr. Hung-wen Liu [email protected] orcid.org/0000-0001-8953-4794 Division of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, University of Texas at Austin, Austin, TX, 78712 USASearch for more papers by this author First published: 15 February 2016 https://doi.org/10.1002/ange.201510635Citations: 6Read the full textAboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract C3′-deoxygenation of aminoglycosides results in their decreased susceptibility to phosphorylation thereby increasing their efficacy as antibiotics. However, the biosynthetic mechanism of C3′-deoxygenation is unknown. To address this issue, aprD4 and aprD3 genes from the apramycin gene cluster in Streptomyces tenebrarius were expressed in E. coli and the resulting gene products were characterized in vitro. AprD4 is shown to be a radical S-adenosylmethionine (SAM) enzyme, catalyzing homolysis of SAM to 5′-deoxyadenosine (5′-dAdo) in the presence of paromamine. [4′-2H]-Paromamine was prepared and used to show that its C4′-H is transferred to 5′-dAdo by AprD4, during which the substrate is dehydrated to a product consistent with 4′-oxolividamine. In contrast, paromamine is reduced to a deoxy product when incubated with AprD4/AprD3/NADPH. These results show that AprD4 is the first radical SAM diol-dehydratase and, along with AprD3, is responsible for 3′-deoxygenation in aminoglycoside biosynthesis. Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Filename Description ange201510635-sup-0001-misc_information.pdf551.3 KB Supplementary Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1S. Magnet, J. Blanchard, Chem. Rev. 2005, 105, 477–498. 10.1021/cr0301088 CASPubMedWeb of Science®Google Scholar 2D. 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