Claisen-type addition of glycine to a pyridoxal iminium ion in water.
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.
Toth
Krisztina
K
Department of Chemistry, University of Buffalo, State University of New York, Buffalo, NY 14260-3000, USA.
Gaskell
Lauren M
LM
Richard
John P
JP
D002625:Chemistry, Organic / Q000379:methods; D002852:Chromatography, Ion Exchange; D005998:Glycine / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007477:Ions; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011730:Pyridoxal / Q000737:chemistry*; D014867:Water
D007477:Ions; D014867:Water; D011730:Pyridoxal; D005998:Glycine