Synthesis of [1-13C] and [1-15N] labelled D1-HomphenylalanineVia a Key Neber Rearrangement

Nigel Peter Botting, MF Oldfield

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10 Citations (Scopus)

Abstract

A synthetic route involving a key Neber rearrangement is described for the preparation of both [1-C-13] and [1-N-15] DL-homophenylalanine (2-amino-4-phenylbutanoic acid), using suitably labelled sodium cyanide as the source of the isotopic label. These compounds have been prepared for use in studies on the biosynthesis of phenylethyl glucosinolate in Brassica napus. 3-Phenylpropanaldoxime, the initial biosynthetic product formed from homophenylalanine, was also prepared in N-15 labelled form.

Original languageEnglish
Pages (from-to)29-36
Number of pages8
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume41
Publication statusPublished - Jan 1998

Keywords

  • glucosinolates
  • Neber rearrangement
  • Brassica
  • homophenylalanine
  • AMINO-ACIDS
  • BIOSYNTHESIS
  • MONOOXYGENASES
  • PLANTS
  • LEAVES

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