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Synthesis of 2,6‐dideoxy‐2‐fluoro‐6‐[ 18 F]‐fluoro‐β‐D‐glucopyranosyl fluoride (2,6FGF) as a potential imaging probe for glucocerebrosidase
Author(s) -
Wong Alexander W.,
Adam Michael J.,
Withers Stephen G.
Publication year - 2001
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.466
Subject(s) - chemistry , hydrolysis , glycoside , yield (engineering) , fluoride , glycoside hydrolase , stereochemistry , in vivo , mannose , biochemistry , inorganic chemistry , metallurgy , biology , materials science , microbiology and biotechnology
We have previously synthesized 2‐deoxy‐2‐[ 18 F]‐fluoro‐β‐mannosyl [ 18 F]‐fluoride and shown that it behaves as a mechanism‐based inhibitor of Agrobacterium sp. β‐glucosidase. In‐vivo experiments indicate that this compound undergoes partial hydrolysis to produce 2‐deoxy‐2‐fluoro‐mannose, which can become phosphorylated and trapped within the cell. We now report the synthesis of another 2‐fluoro glycoside which is 18 F‐labelled at the 6 position so that the label cannot be lost during such glycoside hydrolysis and which, further, cannot be phosphorylated. The mechanism‐based glycosidase inhibitor 2,6‐dideoxy‐2‐fluoro‐6‐[ 18 F]‐fluoro‐β‐D‐glucopyranosyl fluoride (2,6FGF) was synthesized in 69% overall chemical yield and in 9% radiochemical yield (decay corrected) as a potential imaging probe for glycosidase. Copyright © 2001 John Wiley & Sons, Ltd.