Claisen-Type Addition of Glycine to Pyridoxal in Water
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- 作者：Krisztina Toth ; Tina L. Amyes ; John P. Richard ; J. Paul G. Malthouse ; and Má ; ire E. Ní ; Beilliú
- 刊名：Journal of the American Chemical Society
- 出版年：2004
- 出版时间：September 1, 2004
- 年：2004
- 卷：126
- 期：34
- 页码：10538 - 10539
- 全文大小：50K
- 年卷期：v.126,no.34(September 1, 2004)
- ISSN：1520-5126
文摘
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 
lpha.gif" BORDER=0>-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.
lpha.gif" BORDER=0>-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.