Synthesis of [1-11C]D-glucose and [1-11C]D-mannose from on-line produced [11C]nitromethane

Int J Rad Appl Instrum A. 1991;42(9):877-83. doi: 10.1016/0883-2889(91)90228-s.

Abstract

A method for the preparation of [1-11C]D-glucose (III) and [1-11C] D-mannose (IV) from [11C] nitromethane is described. [11C]Nitromethane was produced using the on-line method from [11C]methyl iodide. The condensation of no-carrier-added or carrier-added [11C]nitromethane with D-arabinose to form the intermediate epimeric [1-11C]D-nitro alcohols (I and II) was investigated under various conditions. Compounds I and II were converted to III and IV by the classical Nef reaction with IV as the major product [(IV)/(III) = 3/1-4/1]. The isolated radiochemical yield of III and IV was 25-30% (based on [11C]nitromethane and decay-corrected) and 14-17% (EOB) with a total synthesis time of 50 min, including HPLC-purification. Compounds III and IV were isolated using semi-preparative HPLC and the radiochemical purity was greater than 97%. In a typical run, 1.5-2.0 mCi of III and 6-8 mCi of IV could be isolated (starting from 70-90 mCi [11C]nitromethane).

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Brain / diagnostic imaging
  • Brain / metabolism
  • Carbon Radioisotopes*
  • Chromatography, High Pressure Liquid
  • Glucose / chemical synthesis*
  • Glucose / metabolism
  • Humans
  • Indicators and Reagents
  • Isotope Labeling / methods
  • Magnetic Resonance Spectroscopy
  • Mannose / chemical synthesis*
  • Mannose / metabolism
  • Methane / analogs & derivatives*
  • Nitroparaffins*
  • Tomography, Emission-Computed / methods

Substances

  • Carbon Radioisotopes
  • Indicators and Reagents
  • Nitroparaffins
  • Glucose
  • Methane
  • Mannose
  • nitromethane