Degradation of β-Lactamase Inhibitor, (2S, 3R, 5S)-3-Methyl-7-oxo-3-(1H-1,2,3-triazol-1-yl-methyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid 4,4-Dioxide (YTR-830H), in Aqueous Solutions and Alkaline Methanol Solution : Pathway and Structural Elu

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(2S, 3R, 5S)-3-Methyl-7-oxo-3-(1H-1,2,3-triazol-1-yl-methyl)-4-thia-l-azabicyclo[3.2.0]-heptane-2-carboxylic acid 4,4-dioxide (YTR-830H) is a new β-lactamase inhibitor. The degradation of this β-lactamase inhibitor in several buffer solutions, NaOH aqueous solution and NaOH-saturated methanol solution was investigated. In the initial step of degradation in aqueous solutions, YTR-830H was degraded to 2-amino-3-methyl-3-sulfino-4-(1H-1,2,3-triazol-1-yl)-butyric acid (YTR-830H-II) and formylacetic acid (YTR-830H-III) through (E)-5-methyl-5-sulfino-6-(1H-1,2,3-triazol-1-yl)-3-aza-1-heptene-1,4-dicarboxylic acid (YTR-830H-I) as an intermediate. The YTR-830H-II in all solutions then proceeded to an unidentified product, YTR-830H-IIa. In acidic solution it was converted to 1,2,3-triazole and several unidentified produts (YTR-830H-IIa, -IIb, -IIc and -IId). Degradation at various pHs showed different patterns and rates. Following degradation in NaOH-saturated methanol solution, 1-methyl hydrogen (E)- and (Z)-5-methyl-5-sulfino-6-(1H-1,2,3-triazol-1-yl)-3-aza-1-heptene-1,4-dicarboxylic acid (YTR-830H-Ia and -Ib) were detected.
社団法人日本薬学会の論文
1988-11-25