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

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.

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EXT809.pdf (Publisher version), 628KB
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https://doi.org/10.1016/j.bmc.2013.05.057 (Publisher version)
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 Creators:
Caputi, Lorenzo1, Author           
Rejzek, Martin2, Author
Louveau, Thomas2, Author
O'Neill, Ellis C.2, Author
Hill, Lionel2, Author
Osbourn, Anne2, Author
Field, Robert A.2, Author
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1External Organizations, ou_persistent22              
2external, ou_persistent22              

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Free keywords: SUGAR NUCLEOTIDE; GLYCOSYLTRANSFERASES; PROBES; BIODISTRIBUTION; GLYCOSYLATION; SPECIFICITY; SUBSTRATE; GALACTOSEBiochemistry & Molecular Biology; Pharmacology & Pharmacy; Chemistry; Sugar nucleotide; Biotransformation; Fluorosugar; Glucosyltransferase; Natural product;
 Abstract: 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.

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 Dates: 2013-08-15
 Publication Status: Issued
 Pages: 6
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 Rev. Type: -
 Identifiers: DOI: 10.1016/j.bmc.2013.05.057
Other: EXT809
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Title: Bioorganic & Medicinal Chemistry
  Other : Bioorg. Med. Chem.
Source Genre: Journal
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Publ. Info: Amsterdam, The Netherlands : Elsevier B. V.
Pages: - Volume / Issue: 21 (16) Sequence Number: - Start / End Page: 4762 - 4767 Identifier: ISSN: 0968-0896
CoNE: https://pure.mpg.de/cone/journals/resource/954925582193