105851-17-0Relevant articles and documents
Chemoenzymatic n.c.a synthesis of the coenzyme UDP-2-deoxy-2-( 18F)fluoro-α-D-glucopyranose as substrate of glycosyltransferases
Prante, Olaf,Hamacher, Kurt,Coenen, Heinz H.
, p. 55 - 63 (2007)
The development of 18F-labelling methods adopted to proteins and bioactive peptides is of great interest in radiopharmaceutical sciences. In order to provide 18F-labelled sugars as a polar prosthetic group for an enzymatic 18F-labelling procedure, an appropriate nucleotide activated sugar is needed. Here, we present the radiosynthesis of n.c.a. UDP-2-deoxy-2-[18F]fluoro-α-D-glucopyranose (UDP-[ 18F]FDG) as a substrate for glycosyltransferases. The MacDonald synthesis of [18F]FDG-1-phosphate was successfully combined with an enzymatic activation to obtain UDP-[18F]FDG directly in an aqueous medium located in the void volume of a solid phase cartridge. The radiochemical yield of UDP-[18F]FDG was 20% (based on [18F]fluoride) after a total synthesis time of 110 min. Thus, an intermediate was provided for the enzymatic transfer of [18F]FDG using UDP-[18F]FDG as glycosyl donor making use of a suitable glycosyltransferase. This would represent a highly selective and mild 18F-labelling method for glycosylated biomolecules. Copyright
A new class of SN2 reactions catalyzed by protic solvents: Facile fluorination for isotopic labeling of diagnostic molecules
Kim, Dong Wook,Ahn, Doo-Sik,Oh, Young-Ho,Lee, Sungyul,Kil, Hee Seup,Oh, Seung Jun,Lee, Sang Ju,Kim, Jae Seung,Ryu, Jin Sook,Moon, Dae Hyuk,Chi, Dae Yoon
, p. 16394 - 16397 (2006)
Aprotic solvents are usually preferred for the SN2 reactions, because nucleophilicity and hence SN2 reactivity are severely retarded by the influence of the partial positive charge of protic solvents. In this work, we introduce a remarkable effect of using tertiary alcohols as a reaction medium for nucleophilic fluorination with alkali metal fluorides. In this novel synthetic method, the nonpolar protic tert-alcohol enhances the nucleophilicity of the fluoride ion dramatically in the absence of any kind of catalyst, greatly increasing the rate of the nucleophilic fluorination and reducing formation of byproducts (such as alkenes, alcohols, or ethers) compared with conventional methods using dipolar aprotic solvents. The great efficacy of this method is a particular advantage in labeling radiopharmaceuticals with [18F]fluorine (t1/2 = 110 min) for positron emission tomographic (PET) imaging, and it is illustrated by the synthesis of four [ 18F]fluoride-radiolabeled molecular imaging probes-[ 18F]FDG, [18F]FLT, [18F]FP-CIT, and [ 18F]FMISO-in high yield and purity and in shorter times compared to conventional syntheses.
SYSTEM FOR RADIOPHARMACEUTICAL PRODUCTION
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Page/Page column 41; 44, (2016/06/06)
Certain embodiments of the present invention relate to a system and a method for producing a radiopharmaceutical, wherein the system is formed from and/ or provides a microfluidic flow system. In certain embodiments, the system comprises a radioisotope isolation module, a radiopharmaceutical production module, a purification module and a quality control module.
DEVICE AND METHOD FOR THE PRODUCTION OF RADIOCHEMICAL COMPOUNDS
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Paragraph 0093-0094, (2015/05/26)
The invention relates to a device for the preparation of radiochemical compounds. It is provided that the device comprises at least a reaction module, a dosing module, and a storage module, wherein the reaction module has at least one reaction vessel having a closable opening through which substances needed for the preparation of a predetermined radiochemical compound can be introduced into the reaction vessel of the reaction module and through which the prepared radiochemical compound can be removed from the reaction vessel of the reaction module;the dosing module has at least one pipetting head which can be moved relative to the storage module and the reaction module and in x, y, and z directions and also has at least one dosing unit; andat least one reservoir for one of the substances needed for the preparation of the respective radiochemical compound is formed in the storage module.
DUAL RUN CASSETTE FOR THE SYNTHESIS OF 18F-LABELLED COMPOUNDS
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Page/Page column 15-17, (2015/06/03)
The invention provides a new chemical process, a new cassette configuration, and new software. The invention allows one synthesizer in one hot cell to produce sequentially two batches of [18F]-labelled PET tracer in the same day.
MODULAR RADIOCHEMISTRY SYNTHESIS SYSTEM
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Paragraph 0291-0295, (2016/01/15)
A modular chemical production system includes multiple modules for performing a chemical reaction, particularly of radiochemical compounds, from a remote location. One embodiment comprises a reaction vessel including a moveable heat source with the positi
System, device and method for preparing tracers and transferring materials during radiosynthesis
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Paragraph 0130-0131, (2014/11/13)
A system, apparatus, and method for transferring chemical solutions and synthesizing a tracer. For transferring chemical solutions, the system comprises a primary container; a secondary container; a first line in communication with the primary container a
3,4,6-Tri-O-acetyl-1,2-O-[1-(exo-ethoxy)ethyl-idene]-Β-d-manno- pyranose 0.11-hydrate
Liu, Ya-Ling,Zou, Pei,Wu, Hao,Xie, Min-Hao,Luo, Shi-Neng
, p. o338-o340 (2012/11/13)
The title compound, C16H24O10·0. 11H2O, is a key inter-mediate in the synthesis of 2-de-oxy-2-[ 18F]fluoro-d-glucose (18F-FDG), which is the most widely used mol-ecular-imaging probe for positron emission tomography (PET). The crystal structure has two independent mol-ecules (A and B) in the asymmetric unit, with closely comparable geometries. The pyran-ose ring adopts a 4 C 1 conformation [Cremer-Pople puckering parameters: Q = 0.553 (2) A?, = 16.2 (2)° and = 290.4 (8)° for mol-ecule A, and Q = 0.529 (2) A?, =15.3 (3)° and = 268.2 (9)° for mol-ecule B], and the dioxolane ring adopts an envelope conformation. The chiral centre in the dioxolane ring, introduced during the synthesis of the compound, has an R configuration, with the eth-oxy group exo to the manno-pyran-ose ring. The asymmetric unit also contains one water mol-ecule with a refined site-occupancy factor of 0.222 (8), which bridges between mol-ecules A and B via O - H?O hydrogen bonds.
Homogeneous nucleophilic radiofluorination and fluorination with phosphazene hydrofluorides
Mathiessen, Bente,Jensen, Andreas T. I.,Zhuravlev, Fedor
experimental part, p. 7796 - 7805 (2011/08/22)
A series of phosphazenium hydrofluorides, P1 tBu·[18/19F]HF, P1 tOct·[18/19F]HF, P2Et· [18/19F]HF, and P4tBu·[ 18/19F]HF, was synthesized. The radioactive phosphazenium [ 18F]hydrofluorides were obtained by the one-step formation and trapping of gaseous [18F]HF with the respective phosphazene bases. The [19F] isotopomers were prepared from the corresponding phosphazene bases and Et3N·3HF. Under the design of experiment (DoE)-optimized conditions, P2Et·HF and P 4tBu·HF fluorinated alkyl chlorides, bromides, and pseudohalides in 76-98 % yield, but gave lower yields with iodides and electron-deficient arenes. DoE models showed that fluorination can be performed in glass vessels, and that the reactivity of P2Et· HF and P4tBu·HF is dominated by solvent polarity but is insensitive to water to at least 2 equiv. In contrast, P1 tBu·HF and P1tOct·HF were unstable towards autofluorolysis. DFT calculations were performed to rationalize this finding in terms of diminished steric bulk, higher Parr's electrophilicity, and chemical hardness of P1RH +. The corresponding radiofluorination reaction gave no valid DoE model but displayed similar substrate scope. High specific activity and excellent radiochemical yields with various pseudohalides (81-91 %) suggest that the proposed radiofluorination methodology can complement the current [ 18F]KF/Kryptofix methods, particularly in the areas for which nonpolar reaction conditions are required. A tale of fluoride: Up to 82 % of [18F]fluoride can be recovered from aqueous solution as [ 18F]HF gas in just one step (see scheme; Tf: trifluoromethanesulfonyl, Ms: methanesulfonyl, Ts=p-toluenesulfonyl). Trapped as phosphazenium hydrofluorides, 18F- and 19F- isotopomers attain high nucleophilicity and solubility in nonpolar solvents. Excelling in fluorination and radiofluorination of various pseudohalides, their substrate scope also extends to halides and nitroarenes. Copyright
Synthesis of the positron-emitting radiotracer [18F]-2-fluoro-2- deoxy-d-glucose from resin-bound perfluoroalkylsulfonates
Brown, Lynda J.,Ma, Nianchun,Bouvet, Denis R.,Champion, Sue,Gibson, Alex M.,Hu, Yulai,Jackson, Alex,Khan, Imtiaz,Millot, Nicolas,Topley, Amy C.,Wadsworth, Harry,Wynn, Duncan,Brown, Richard C. D.
experimental part, p. 564 - 575 (2009/07/18)
A new approach to the synthesis of 2-fluoro-2-deoxy-d-glucose (FDG, [ 19/18F]-3) is described, which employs supported perfluoroalkylsulfonate precursors 33-36, where the support consists of insoluble polystyrene resin beads. Treatment of these resins with [ 19F]fluoride ion afforded protected FDG [19F]-18 as the major product, and the identities of the main byproducts were determined. Acidic removal of the acetal protecting groups from [19F]-18 was shown to produce [19F]FDG. The method has been applied to the efficient radiosynthesis of the imaging agent [18F]FDG, and was shown to produce the radiochemical tracer in good radiochemical yield (average 73%, decay corrected). The Royal Society of Chemistry 2009.
