A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate

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Caputi, Lorenzo, Rejzek, Martin, Louveau, Thomas, O'Neill, Ellis C., Hill, Lionel, Osbourn, Anne and Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 (2013) A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate. Bioorganic and Medicinal Chemistry, 21 (16). pp. 4762-4767. ISSN 0968-0896

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Abstract

In connection with prospective 18F-PET imaging studies, the potential for enzymatic synthesis of fluorine-labelled glycosides of small molecules was investigated. Approaches to the enzymatic synthesis of anomeric phosphates of d-gluco-configured fluorosugars proved ineffective. In contrast, starting in the d-galacto series and relying on the consecutive action of Escherichia coli galactokinase (GalK), galactose-1-phosphate uridylyltransferase (GalPUT), uridine-5′-diphosphogalactose 4-epimerase (GalE) and oat root glucosyltransferase (SAD10), a quick and effective synthesis of 6-deoxy-6-fluoro-d-glucosyl N-methylanthranilate ester was achieved.

Item Type: Article
Additional Information: Funding Information: This work was supported by the UK BBSRC Institute Strategic Programme Grant on Understanding and Exploiting Metabolism (MET) [BB/J004561/1] and the John Innes Foundation .
Uncontrolled Keywords: biotransformation,fluorosugar,glucosyltransferase,natural product,sugar nucleotide,biochemistry,molecular medicine,molecular biology,pharmaceutical science,drug discovery,clinical biochemistry,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1300/1303
Faculty \ School:
Faculty of Science > School of Biological Sciences
Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
Related URLs:
Depositing User: LivePure Connector
Date Deposited: 04 Sep 2024 13:36
Last Modified: 25 Sep 2024 18:06
URI: https://ueaeprints.uea.ac.uk/id/eprint/96546
DOI: 10.1016/j.bmc.2013.05.057

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