Glucose 6-phosphate, 2-deoxy-2- fluoro

Deoxy-3-fluoro-D-glucose 3-deoxy-3-fluoro-D-glucose 6-phosphate 20 86 HK 14 PK 18 70... 

Deoxy-3-fluoro-D-glucose (see Section 11,2), a weak substrate for yeast hexokinase, is phosphorylated enzymically - to give the 6-phosphate 588, which is transformed into 2-deoxy-2-fluoro-D-arabinose 5-phos-phate (589) by lead tetraacetate oxidation. 

In fluorine-18 chemistry some enzymatic transformations of compounds already labelled with fluorine-18 have been reported the synthesis of 6-[ F] fluoro-L-DOPA from 4-[ F]catechol by jS-tyrosinase [241], the separation of racemic mixtures of p F]fluoroaromatic amino acids by L-amino acylase [242] and the preparation of the coenzyme uridine diphospho-2-deoxy-2-p F]fluoro-a-o-glucose from [ F]FDG-1-phosphate by UDP-glucose pyrophosphorylase [243]. In living nature compounds exhibiting a carbon-fluorine bond are very rare. 

The syntheses of sucrose 6 -phosphate, methyl a-mannopyranoside 4- and 6-phosphates, and 3-deoxy-3-fluoro-D-glucose 1- and 6-phosphates [ (57) and (58) ] have been described. Neither (57) nor (58) was a substrate for UDPGlc-pyrophosphorylase or phosphoglucomutase, although (58) was a poor substrate for glucose 6-phosphate dehydrogenase. ... 

We have developed preparative enzymatic syntheses of several unusual hexoketoses using fructose-1,6-diphosphate aldolase (FDP-aldolase, E.C.4.1.2.13) as catalyst and dihydroxyacetone phosphate (DHAP) and an aldehyde as substrates (15). The enzyme appears to be very specific for DHAP but will accept a variety of aldehydes as acceptors. The ketose-1-phosphates prepared are converted to the phosphate free ketoses after removal of the phosphate group by acid- or phosphatase-catalyzed hydrolysis. The ketoses can be isomerized stereospecifically to aldoses catalyzed by glucose isomerase (E.C.5.3.1.5.) from Flavobacteriuum arborescens. The equilibrium mixtures of aldoses and ketoses are then separated by chromatography on Dowex 50 (Ba ) or Dowex 1 (HSO "). Figure 1 illustrates the preparation of a mixture of 6-deoxy-6-fluoro-D-fructose... 

Figure 6. High performance liquid chromatogram if F-18 in rat heart rate after Injection of 3-deoxy-3-fluoro-D-glucose. Stationary phase, anion-exchange bonded silica mobile phase, 20nM potassium phosphate, PH 4.5 Peak assignments in order of elution 3FDG, unknown, unknown, 3FDG-6-phosphate. (Reproduced with permission from Ref. 49. Copyright 1984 American Physiological Society.)...

Fig. 33.2. F-2-fluoro-2-deoxy-D-glucose (FDG) is actively taken up by glucose transport proteins into the cell. Within the cell, FDG is metabolized to FDG-6-phosphate, which is metabolically trapped...

The metabolic interconversion of 2-deoxy-2-fluoro-D glucose and 2-deoxy-2-fluoro-D-mannose (and their 6-phosphates) in tumour cells was investigated by F - NMR spectroscopy, and a mannose glucose equilibrium ratio of -4 1 was observed.The conversion of 2-deoxy-2-fluoro-D-galactose into its aluco-isomer via the action of a UDP-galactose epimerase has been observed in vivo in mice by use of F - NMR spectroscopy ... 

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