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beta-Configured clickable [F-18] FDGs as novel F-18-fluoroglycosylation tools for PET
Linkopings Univ, IFM Dept Biol Chem & Phys, S-58183 Linkoping, Sweden..
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
Linkopings Univ, IFM Dept Biol Chem & Phys, S-58183 Linkoping, Sweden..
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Molecular Imaging.
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2017 (English)In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 41, no 18, p. 10231-10236Article in journal (Refereed) Published
Abstract [en]

In oncology and neurology the F-18-radiolabeled glucose analogue 2-deoxy-2-[F-18]fluoro-D-glucose ([F-18]FDG) is by far the most commonly employed metabolic imaging agent for positron emission tomography (PET). Herein, we report a novel synthetic route to beta-configured mannopyranoside precursors and a chemoselective F-18-fluoroglycosylation method that employ two b-configured [F-18]FDG derivatives equipped with either a terminal azide or alkyne aglycon respectively, for use as a CuAAC clickable tool set for PET. The b-configured precursors provided the corresponding [F-18]FDGs in a radiochemical yield of 77-88%. Further, the clickability of these [F-18]FDGs was investigated by click coupling to the suitably functionalized Fmoc-protected amino acids, Fmoc-N-(propargyl)-glycine and Fmoc-3-azido-L-alanine, which provided the F-18-fluoroglycosylated amino acid conjugates in radiochemical yields of 75-83%. The F-18-fluoroglycosylated amino acids presented herein constitute a new and interesting class of metabolic PET radiotracers.

Place, publisher, year, edition, pages
ROYAL SOC CHEMISTRY , 2017. Vol. 41, no 18, p. 10231-10236
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Chemical Sciences
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URN: urn:nbn:se:uu:diva-336822DOI: 10.1039/c7nj00716gISI: 000411767400073OAI: oai:DiVA.org:uu-336822DiVA, id: diva2:1168204
Funder
Swedish Foundation for Strategic Research Swedish Research Council
Available from: 2017-12-20 Created: 2017-12-20 Last updated: 2017-12-20Bibliographically approved

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Nordeman, PatrikAntoni, Gunnar
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Organic Pharmaceutical ChemistryDivision of Molecular Imaging
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