65 ブレオマイシンのβ-lactam環の化学的証明

概要

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Treatment of bleomycin (1) with 10% acetic acid in water under reflux for 5 hrs. afforded (5) as a major degradation product. The structure of (5) was deduced from its properties and comparison of its pKa values with those of model compounds (Table 2). Formation of (5) can be interpreted only by the presence of β-lactam moiety in bleomycin molecule. (Fig. 4). Pyruvamide was actually isolated from the degradation products. From informations obtained in the studies of (5), reaction conditions to yield (6) and its isolation procedure were suggested. Actually, (6) appeared in the expected fraction of chromatography of degradation products, which were yielded by treatment for 48 hrs. at 50℃ in 10% acetic acid. The structure of (6) was confirmed by chemical and spectroscopic studies. Isolation of (6) is the direct proof for the β-lactam structure of bleomycin. Significance of the β-lactam moiety for the biological activity was elucidated by these studies.
天然有機化合物討論会の論文
1975-10-01