Fluorinated sugar analogues have proven useful in probing the substrate specificity and roles of sugar processing enzymes and transporters.  To synthesize a fluorinated sucrose analogue for plant studies, sucrose 2,3,4,6,3',4',6'-hepta-O-acetate was prepared by regioselective mono-deacetylation of commercially-available sucrose octaacetate, using an industrial esterase enzyme.  The resultant sucrose heptaacetate was then converted to the corresponding triflate.  Reaction of this triflate precursor with either tetrabutylammonium fluoride or with [18F]fluoride, followed by base hydrolysis to remove the acetate groups, gave either 1'-fluoro-1'-deoxysucrose or the corresponding radiofluorinated compound respectively, the latter in 26 % radiochemical yield.  A second radiofluorinated dissacharide sugar, 6-[18F]fluoro-6-deoxytrehalose was prepared using a similar strategy.  This study demonstrates the use of an enzymatic approach to aid synthesis of regiospecific fluorination and radiofluorination precursors starting from the readily available fully-acetylated sugars, thus avoiding the need for a complex classical carbohydrate protection strategy to individually protect each hydroxyl group in the molecule.

Chemo-enzymatic synthesis of fluorinated and radiofluorinated dissacharide sugars for in vivo plant studies

245th National Meeting (2013)

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