Degradation of Clavulanic Acid in Aqueous Alkaline Solution : Isolation and Structural Investigation of Degradation Products

概要

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The degradation of potassium clavulanate in a weakly alkaline aqueous solution has been investigated. Potassium clavulanate was degraded in 0.1 M Na_2HPO_4 solution at various temperatures. Four degradation products were isolated and their structures were elucidated as 2,5-bis-(2-hydroxyethyl) pyrazine (I), 3-methyl-2,5-bis-(2-hydroxyethyl) pyrazine (II), 3-(2-carboxyethyl)-2,5-bis-(2-hydroxyethyl) pyrazine (III). and 3-ethyl-2.5-bis-(2-hydroxyethyl) pyrazine (IV) by mass spectroscopy and nuclear magnetic resonance spectroscopy. High-performance liquid chromatographic analysis of the reaction solution indicated that the reaction at 60℃ yielded all four pyrazine derivatives, whereas II was not formed at 35℃ and III was not formed at 100℃. A reaction mechanism is proposed which involves 4-amino-3-oxobutanol (IX) as a key intermediate.
社団法人日本薬学会の論文
1985-01-25