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.
Original language | English (US) |
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Pages (from-to) | 1449-1458 |
Number of pages | 10 |
Journal | Applied Radiation and Isotopes |
Volume | 44 |
Issue number | 12 |
DOIs | |
State | Published - Dec 1993 |
Externally published | Yes |
ASJC Scopus subject areas
- Radiation