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beta-Configured cli...
beta-Configured clickable [F-18] FDGs as novel F-18-fluoroglycosylation tools for PET
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- Elgland, Mathias, 1987- (author)
- Linköpings universitet,Kemi,Tekniska fakulteten,Linkopings Univ, IFM Dept Biol Chem & Phys, S-58183 Linkoping, Sweden.
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- Nordeman, Patrik (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi,Uppsala University, Sweden
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- Fyrner, Timmy, 1981- (author)
- Linköpings universitet,Kemi,Tekniska fakulteten,Linkopings Univ, IFM Dept Biol Chem & Phys, S-58183 Linkoping, Sweden.
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- Antoni, Gunnar (author)
- Uppsala universitet,Avdelningen för Molekylär Avbildning,Uppsala University, Sweden
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- Nilsson, Peter, 1970- (author)
- Linköpings universitet,Kemi,Tekniska fakulteten,Linkopings Univ, IFM Dept Biol Chem & Phys, S-58183 Linkoping, Sweden.
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- Konradsson, Peter, 1957- (author)
- Linköpings universitet,Kemi,Tekniska fakulteten,Linkopings Univ, IFM Dept Biol Chem & Phys, S-58183 Linkoping, Sweden.
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(creator_code:org_t)
- 2017
- 2017
- English.
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In: New Journal of Chemistry. - : ROYAL SOC CHEMISTRY. - 1144-0546 .- 1369-9261. ; 41:18, s. 10231-10236
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Abstract
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- 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.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Publication and Content Type
- ref (subject category)
- art (subject category)
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