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dc.contributor.authorFeng, Xuan
dc.contributor.authorBello, Davide
dc.contributor.authorLowe, Phillip T.
dc.contributor.authorClark, Joshua
dc.contributor.authorO'Hagan, David
dc.date.accessioned2019-11-11T10:30:11Z
dc.date.available2019-11-11T10:30:11Z
dc.date.issued2019-11-07
dc.identifier.citationFeng , X , Bello , D , Lowe , P T , Clark , J & O'Hagan , D 2019 , ' Two 3′-O-β-glucosylated nucleoside fluorometabolites related to nucleocidin in Streptomyces calvus ' , Chemical Science , vol. 10 , no. 41 , pp. 9501-9505 . https://doi.org/10.1039/c9sc03374ben
dc.identifier.issn2041-6520
dc.identifier.otherPURE: 263041346
dc.identifier.otherPURE UUID: 2ba33722-dfd8-4e9c-9d1b-7a46ca725ff5
dc.identifier.otherScopus: 85074230437
dc.identifier.otherORCID: /0000-0002-0510-5552/work/68281309
dc.identifier.otherWOS: 000492396300007
dc.identifier.otherORCID: /0000-0003-1568-0750/work/122719948
dc.identifier.urihttp://hdl.handle.net/10023/18896
dc.descriptionAuthors thank the EPSRC Catalysis HUB (University of Manchester) for financial support. We also thank Roger Howard, Usa Reilly, Jeffery Janso and Alessandra Eustaquio at the Biocatalysis Technologies Laboratory, Pfizer, Groton, USA, for financial support, a producing strain of S. calvus, and supporting the research with genome sequencing.en
dc.description.abstractThe antibiotic nucleocidin is a product of the soil bacterium Streptomyces calvus T-3018. It is among the very rare fluorine containing natural products but is distinct from the other fluorometabolites in that it is not biosynthesised from 5′-fluorodeoxyadenosine via the fluorinase. It seems to have a unique enzymatic fluorination process. We disclose here the structures of two 4′-fluoro-3′-O-β-glucosylated metabolites (F-Mets I and II) which appear and then disappear before nucleocidin production in batch cultures of S. calvus. Full genome sequencing of S. calvus T-3018 and an analysis of the putative biosynthetic gene cluster for nucleocidin identified UDP-glucose dependent glucosyl transferase (nucGT) and glucosidase (nucGS) genes within the cluster. We demonstrate that these genes express enzymes that have the capacity to attach and remove glucose from the 3′-O-position of adenosine analogues. In the case of F-Met II, deglucosylation with the NucGS glucosidase generates nucleocidin suggesting a role in its biosynthesis. Gene knockouts of nucGT abolished nucelocidin production.
dc.format.extent5
dc.language.isoeng
dc.relation.ispartofChemical Scienceen
dc.rightsCopyright © 2019 The Author(s). Open Access Article. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.en
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleTwo 3′-O-β-glucosylated nucleoside fluorometabolites related to nucleocidin in Streptomyces calvusen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.identifier.doihttps://doi.org/10.1039/c9sc03374b
dc.description.statusPeer revieweden


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