| 1. |
- Andersen, Thomas L., et al.
(författare)
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Application of Methyl Bisphosphine-Ligated Palladium Complexes for Low Pressure N-C-11-Acetylation of Peptides
- 2017
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Ingår i: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 56:16, s. 4549-4553
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Tidskriftsartikel (refereegranskat)abstract
- A mild and effective method is described for C-11-labeling of peptides selectively at the N-terminal nitrogen or at internal lysine positions. The presented method relies on the use of specific biphosphine palladium-methyl complexes and their high reactivity towards amino-carbonylation of amine groups in the presence [C-11] carbon monoxide. The protocol facilitates the production of native N-C-11-acetylated peptides, without any structural modifications and has been applied to a selection of bioactive peptides.
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| 2. |
- Andersen, Thomas L., et al.
(författare)
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Efficient C-11-Carbonylation of Isolated Aryl Palladium Complexes for PET : Application to Challenging Radiopharmaceutical Synthesis
- 2015
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Ingår i: Journal of the American Chemical Society. - : American Chemical Society (ACS). - 0002-7863 .- 1520-5126. ; 137:4, s. 1548-1555
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Tidskriftsartikel (refereegranskat)abstract
- We describe the successful implementation of palladium-aryl oxidative addition complexes as stoichiometric reagents in carbonylation reactions with (CO)-C-11 to produce structurally challenging, pharmaceutically relevant compounds. This method enables the first C-11-carbonyl labeling of an approved PET tracer, [C-11]raclopride, for the dopamine D2/D3 receptor by carbonylation with excellent radiochemical purity and yield. Two other molecules, [C-11]olaparib and [C-11]JNJ 31020028, were efficiently labeled in this manner. The technique distinguishes itself from existing methods by the markedly improved purity profiles of the tracer molecules produced and provides access to complex structures in synthetically useful yields, hereby offering a viable alternative to other C-11-labeling strategies.
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| 3. |
- Bergman, Sara, et al.
(författare)
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Synthesis of 11C-Labelled Ureas by Palladium(II)-Mediated Oxidative Carbonylation
- 2017
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Ingår i: Molecules. - : MDPI AG. - 1431-5157 .- 1420-3049. ; 22:10
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Tidskriftsartikel (refereegranskat)abstract
- Positron emission tomography is an imaging technique with applications in clinical settings as well as in basic research for the study of biological processes. A PET tracer, a biologically active molecule where a positron-emitting radioisotope such as carbon-11 has been incorporated, is used for the studies. Development of robust methods for incorporation of the radioisotope is therefore of the utmost importance. The urea functional group is present in many biologically active compounds and is thus an attractive target for incorporation of carbon-11 in the form of [C-11] carbon monoxide. Starting with amines and [C-11] carbon monoxide, both symmetrical and unsymmetrical C-11-labelled ureas were synthesised via a palladium(II)-mediated oxidative carbonylation and obtained in decay-corrected radiochemical yields up to 65%. The added advantage of using [C-11] carbon monoxide was shown by the molar activity obtained for an inhibitor of soluble epoxide hydrolase (247 GBq/mu mol-319 GBq/mu mol). DFT calculations were found to support a reaction mechanism proceeding through an C-11-labelled isocyanate intermediate.
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| 4. |
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| 5. |
- Cortés González, Miguel A., et al.
(författare)
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Rhodium-mediated 18F-oxyfluorination ofdiazoketones using a fluorine-18-containing hypervalent iodine reagent
- 2019
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Ingår i: Chemical Communications. - : Royal Society of Chemistry (RSC). - 1359-7345 .- 1364-548X. ; 55:89, s. 13358-13361
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Tidskriftsartikel (refereegranskat)abstract
- Geminal 18F-oxyfluorination of diazoketones was performed in the presence of rhodium mediators. The reactions were performed using a hypervalent iodine-based [18F]fluoro-benziodoxole reagent. By this methodology various α-[18F]fluoro ethers were obtained in high radiochemical yield (up to 98%) and molar activity (216 GBq μmol-1).
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| 6. |
- Dahl, Kenneth, et al.
(författare)
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11C-Acetylation of Amines with [11C]Methyl Iodide with Bis(cyclopentadienyldicarbonyliron) as the CO Source
- 2017
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Ingår i: European Journal of Organic Chemistry. - : Wiley. - 1434-193X .- 1099-0690. ; :38, s. 5785-5788
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Tidskriftsartikel (refereegranskat)abstract
- We describe herein a novel approach for the direct 11C-acetylation of amines. The carbonylative protocol is palladium-mediated, uses bis(cyclopentadienyldicarbonyliron) as the CO source, and [11C]methyl iodide or [11C]methyl iodide-D3 as a radioactive precursor. A set of functionalized primary and secondary amines was 11C-labelled in radiochemical yields ranging from 7–85 %. The potential use of this method for positron emission tomography radiotracer production was additionally demonstrated by the radiosynthesis of [11C]lacosamide, [11C]melatonine, and [11C]acecainide in 44–55 % RCY.
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| 7. |
- Dahl, Kenneth, et al.
(författare)
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C-11-Carbonylation through in Situ Generated C-11-Benzoyl Chlorides with Tetrabutylammonium Chloride as Chloride Source
- 2017
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Ingår i: European Journal of Organic Chemistry. - : WILEY-V C H VERLAG GMBH. - 1434-193X .- 1099-0690. ; :18, s. 2648-2651
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Tidskriftsartikel (refereegranskat)abstract
- Aromatic C-11-containing acids, amides, esters, and aldehydes were obtained through a novel C-11-carbonylative reaction. In the two-step process, aryl iodides are first reacted with (CO)-C-11 and tetrabutylammonium chloride in a palladium-mediated reaction to yield C-11-benzoyl chlorides in situ. The crude mixture is then further treated with either a hydroxide, amine, alcohol, or a hydride in a second vial to furnish the final C-11-carbonyl product. The monodentate ligand tri-tert-butylphosphonium tetrafluoroborate was proven to be crucial for obtaining high radiochemical yields (RCY). A wide range of C-11-containing carbonyl compounds were successfully radiolabeled in moderate to excellent RCYs, ranging from 41-93%. The synthetic retinoic acid tamibarotene was obtained in a RCY of 89%, whereas the Boc-protected procainamide was labelled in 68% RCY, which is a significantly increase (2-3 fold) in RCY compared to other published methods.
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| 8. |
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| 9. |
- Elgland, Mathias, 1987-, et al.
(författare)
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beta-Configured clickable [F-18] FDGs as novel F-18-fluoroglycosylation tools for PET
- 2017
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Ingår i: New Journal of Chemistry. - : ROYAL SOC CHEMISTRY. - 1144-0546 .- 1369-9261. ; 41:18, s. 10231-10236
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Tidskriftsartikel (refereegranskat)abstract
- 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.
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| 10. |
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