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Claisen-type addition of glycine to pyridoxal in water
Krisztina Toth1, Tina L Amyes, John P Richard
1Department of Chemistry, University at Buffalo, SUNY, Buffalo, New York 14260-3000, USA.
Abstract:
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.
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