Claisen-type addition of glycine to a pyridoxal iminium ion in water

J Org Chem. 2006 Sep 1;71(18):7094-6. doi: 10.1021/jo061090e.

Abstract

The 5'-deoxypyridoxal stabilized glycine carbanion has been generated in water at neutral and mildly basic pH. At pH < 7, this carbanion reacts mainly with the carbonyl carbon of 1 to form a stable Claisen-type adduct. At pH > or = 8, this carbanion reacts with the iminium carbon of the pyridoxal-glycine iminium ion to form the second Claisen-type adduct 3 as the major reaction product.

Publication types

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

MeSH terms

  • Chemistry, Organic / methods
  • Chromatography, Ion Exchange
  • Glycine / chemistry*
  • Hydrogen-Ion Concentration
  • Ions
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Pyridoxal / chemistry*
  • Water

Substances

  • Ions
  • Water
  • Pyridoxal
  • Glycine