Claisen-type addition of glycine to pyridoxal in water.
The reaction between 5'-deoxypyridoxal and glycine in D2O buffered at pD 7.0 does not result in significant formation of the expected products of pyridoxal-catalyzed transamination or deuterium exchange of the alpha-amino protons of glycine, but rather gives a quantitative yield of the two diastereomeric products of the formal Claisen-type addition of glycine to 5'-deoxypyridoxal. The unexpected extensive formation of these products reflects the extraordinary selectivity of the 5'-deoxypyridoxal-stabilized glycine enolate toward addition to the carbonyl group of 5'-deoxypyridoxal in the protic solvent water.
Toth
Krisztina
K
Department of Chemistry, University at Buffalo, SUNY, Buffalo, New York 14260-3000, USA.
Amyes
Tina L
TL
Richard
John P
JP
Malthouse
J Paul G
JP
NíBeilliú
Máire E
ME
D000409:Alanine / Q000031:analogs & derivatives / Q000737:chemistry; D005998:Glycine / Q000737:chemistry*; D011732:Pyridoxal Phosphate / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D014867:Water; D011732:Pyridoxal Phosphate; D000409:Alanine; D005998:Glycine