Synthesis of polymer-bound 6-thiolatomercury and 6-mercuric sulfonate DOPA precursors and their halodemercuration reactivity

Nucl Med Biol. 1995 Jan;22(1):37-43. doi: 10.1016/0969-8051(94)00079-y.

Abstract

Fluorodemercuration has the greatest utility for the preparation of 6-[18F]DOPA, but requires separation from unreacted mercury precursor and other mercury-containing compounds. One approach is the development of a polymer-bound mercury precursor. In this study, polymer-bound 6-thiolatomercury and 6-mercuric sulfonate DOPA derivatives, and its monomeric analogs were synthesized. Fluorodemercuration of monomeric analog of mercuric sulfonate gave half the yield (14-15%) while iododemercuration gave the same yield (38%) compared with a 6-mercuric trifluoroacetate protected DOPA. The mercuric sulfonate undergoes halodemercuration, so polymer-bound halodemercuration precursors may be useful as precursors of 6-[18F]DOPA.

MeSH terms

  • Dihydroxyphenylalanine / analogs & derivatives*
  • Dihydroxyphenylalanine / chemical synthesis
  • Dihydroxyphenylalanine / metabolism
  • Mercury Compounds / metabolism*
  • Polymers
  • Prodrugs / chemical synthesis*
  • Prodrugs / metabolism
  • Sulfates / metabolism*

Substances

  • Mercury Compounds
  • Polymers
  • Prodrugs
  • Sulfates
  • fluorodopa F 18
  • Dihydroxyphenylalanine
  • mercuric sulfate