Synthesis and tritium radiolabelling of fluorinated analogues of myo-inositol

Abstract

Syntheses have been developed for a set of six myo-inositol analogues from myo-inositol in which single hydroxy groups have been replaced by fluorine (monodeoxy-fluoro-myo-inositols). Except for 2-deoxy-2-fluoro-myo-inositol 32 and lD-4-deoxy-4-fluoro-myo-inositol 23, the monodeoxy-fluoro-myo-inositols were substrates for the enzyme inositol dehydrogenase [EC 1.1.1.18], which catalyses the oxidation of the axial 2-position of myo-inositol to give scyllo-inosose. This enzyme was used to exchange tritium radiolabel from myo-[2-³H]inositol to the monodeoxy-fluoro-myo-inositol. 1D-4-Deoxy-4-fluoro-myo-inositol and 2-deoxy-2-fluoro-myo-inositol were radiolabelled chemically.