An enzymatic Finkelstein reaction: fluorinase catalyses direct halogen exchange

Org Biomol Chem. 2019 Aug 28;17(32):7493-7496. doi: 10.1039/c9ob01625b. Epub 2019 Jul 31.

Abstract

The fluorinase enzyme from Streptomyces cattleya is shown to catalyse a direct displacement of bromide and iodide by fluoride ion from 5'-bromodeoxyadenosine (5'-BrDA) and 5'-iododeoxyadenosine (5'-IDA) respectively to form 5'-fluorodeoxyadenosine (5'-FDA) in the absence of l-methionine (l-Met) or S-adenosyl-l-methionine (SAM). 5'-BrDA is the most efficient substrate for this enzyme catalysed Finkelstein reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacterial Proteins / chemistry*
  • Catalysis
  • Deoxyadenosines / chemistry*
  • Halogens / chemistry*
  • Kinetics
  • Methionine / chemistry
  • Molecular Conformation
  • Oxidoreductases / chemistry*
  • S-Adenosylmethionine / chemistry
  • Streptomyces / enzymology
  • Thermodynamics

Substances

  • Bacterial Proteins
  • Deoxyadenosines
  • Halogens
  • S-Adenosylmethionine
  • Methionine
  • Oxidoreductases
  • fluorinase
  • 2'-deoxyadenosine