18 F-Trifluoromethylation of Unmodified Peptides with 5- 18 F-(Trifluoromethyl)dibenzothiophenium Trifluoromethanesulfonate

J Am Chem Soc. 2018 Feb 7;140(5):1572-1575. doi: 10.1021/jacs.7b10227. Epub 2018 Jan 22.

Abstract

The 18F-labeling of 5-(trifluoromethyl)-dibenzothiophenium trifluoromethanesulfonate, commonly referred to as the Umemoto reagent, has been accomplished applying a halogen exchange 18F-fluorination with 18F-fluoride, followed by oxidative cyclization with Oxone and trifluoromethanesulfonic anhydride. This new 18F-reagent allows for the direct chemoselective 18F-labeling of unmodified peptides at the thiol cysteine residue.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fluorine Radioisotopes / chemistry
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Molecular Structure
  • Peptides / chemistry*

Substances

  • Fluorine Radioisotopes
  • Hydrocarbons, Fluorinated
  • Peptides