The Synthesis of 5-Fluorokynurenine and 6-Fluorokynurenic Acid as Metabolic Probes

KM Muirhead, Nigel Peter Botting

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

(2S)-5-Fluorokynurenine 9 and 6-fluorokynurenic acid 14 were synthesised as fluorinated probes to enable the metabolism of kynurenine to be monitored in vivo by F-19 NMR spectroscopy. The ( 2S)-5-fluorokynurenine 9 was prepared using a Friedel-Crafts acylation of N-((t)butoxycarbonyl)-4-fluoroaniline with a chiral oxazolidine derivative 6, derived from 2S-aspartic acid. This represents a novel, and simple, method for the synthesis of kynurenine derivatives. The 6-fluorokynurenic acid 14 was synthesised using a Conrad-Limpach type synthesis. Preliminary biological studies are described.

Original languageEnglish
Pages (from-to)37-45
Number of pages9
JournalARKIVOC
Volume3
Publication statusPublished - 2002

Keywords

  • 5-fluorokynurenine
  • 6-fluorokynurenic acid
  • metabolic probes
  • Conrad-Limpach type synthesis
  • RAT-BRAIN
  • POTENT

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