Synthesis of 6-[18F] and 4-[18F]fluoro-L-m-tyrosines via regioselective radiofluorodestannylation

Appl Radiat Isot. 1993 Mar;44(3):527-36. doi: 10.1016/0969-8043(93)90165-7.

Abstract

The regioselective radiofluorodestannylation of 6-trimethylstannyl-L-m-tyrosine derivative 6 with [18F]F2 and [18F]acetyl hypofluorite afforded, after acid hydrolysis, 6-[18F]fluoro-L-m-tyrosine (8a) in radiochemical yields of 23 and 17%, respectively. Similarly, 4-[18F]fluoro-L-m-tyrosine (13a) was synthesized in 11% radiochemical yield from the corresponding 4-trimethylstannyl-L-m-tyrosine derivative 11 using [18F]F2. The structural analyses of precursors (6,11), intermediates, and the final products (after 18F decay), were carried out by 1H, 13C, 19F, 119Sn-NMR and high resolution mass spectroscopy.

Publication types

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

MeSH terms

  • Fluorine Radioisotopes
  • Tyrosine / analogs & derivatives*
  • Tyrosine / chemical synthesis

Substances

  • Fluorine Radioisotopes
  • 4-fluoro-3-tyrosine
  • 6-fluoro-3-tyrosine
  • Tyrosine