Radiosynthesis of 6-[C-11]-d-glucose

J. R. Grierson, J. E. Biskupiak, J. M. Link, K. A. Krohn

Research output: Contribution to journalArticle

11 Scopus citations

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 languageEnglish (US)
Pages (from-to)1449-1458
Number of pages10
JournalApplied Radiation and Isotopes
Volume44
Issue number12
DOIs
StatePublished - Dec 1993

ASJC Scopus subject areas

  • Radiation

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