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

Caputi, Lorenzo; Rejzek, Martin; Louveau, Thomas; O'Neill, Ellis C.; Hill, Lionel; Osbourn, Anne; Field, Robert A.

doi:10.1016/j.bmc.2013.05.057

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

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https://doi.org/10.1016/j.bmc.2013.05.057
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Caputi, L., Rejzek, M., Louveau, T., O'Neill, E. C., Hill, L., Osbourn, A., et al. (2013). A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate. Bioorganic & Medicinal Chemistry, 21(16), 4762-4767. doi:10.1016/j.bmc.2013.05.057.

Zitierlink: https://hdl.handle.net/21.11116/0000-0009-C837-8

Zusammenfassung

In connection with prospective F-18-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 colt 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. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.