title: Radiosynthesis of 6-[C-11]-D-glucose.
abstract: Availability of 6-[C-11]-D-glucose will permit positron emission tomography (PET) investigations of glucose utilization derived from the pentose shunt which supports biosynthesis in tissues. The first radiosynthesis of 6-[C-11]-D-glucose is described. As much as 1 mCi of 6-[C-11]-D-glucose, sufficient for animal studies, is obtained from [C-11]CO2 after 100 min with a 16% radiochemical yield (EOB). The radiosynthesis has many attractive features. The method uses [C-11]CH3I and combines a Wittig reaction and a stereoselective OsO4 catalyzed alkene hydroxylation. The OsO4 hydroxylation of the [C-11]-labeled alkene (9) is accomplished in less than 10 min with high stereoselectivity (94:6) in favor of the 6-[C-11]-D-gluco-isomer. HPLC purification (C-18) of the protected labeled sugar removes the undesired 6-[C-11]-L-ido-sugar at an early stage and avoids the use of an expensive low-capacity ion-exchange HPLC column. OsO4, a highly toxic reagent, is removed in the process by adsorption and inactivation on polymer-bound triphenylphosphine.
authors.affiliation: School of Medicine, Department of Radiology, University of Washington, Seattle 98195.
authors.forename: J R
authors.initials: JR
authors.lastname: Grierson
authors.forename: J E
authors.initials: JE
authors.lastname: Biskupiak
authors.forename: J M
authors.initials: JM
authors.lastname: Link
authors.forename: K A
authors.initials: KA
authors.lastname: Krohn
mesh_terms: D002250:Carbon Radioisotopes; D005947:Glucose; D007553:Isotope Labeling / Q000379:methods*
chemical_list: D002250:Carbon Radioisotopes; D005947:Glucose