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本文报导新的半合成氨基糖甙抗菌素BB K8(Ⅰ)的化学合成、结构及生物学性质。Ⅰ为1-N-〔L(-)-4-氨基-2-羟基丁酰〕卡那霉素A。合成途径:卡那霉素A先与N-(苄氧碳酰氧基)-丁二酰亚胺反应生成6′-N-苄氧碳酰卡那霉素A,后者与等克分子的L(-)-4-苄氧碳酰氨基-2-羟基丁酸N-羟基丁二酰亚胺酯缩合,经氢解除去保护基团即得Ⅰ。Ⅰ用过碘酸氧化降解生成1-N-L(-)-4-氨基2-羟基丁酰-2-脱氧链霉胺,Ⅰ与对-甲氧基苯甲醛反应生成的Schiff碱用NaBH_4还原降解生成3-N-对-甲氧基苄基-2-脱氧链霉胺,以上两个降解产物与从butirosin A所得的相应产物相同,证明L(-)-4-氨基-
This paper reports the chemical synthesis, structure and biological properties of a novel semi-synthetic aminoglycoside antibiotic BB K8 (Ⅰ). I is 1-N- [L (-) - 4-amino-2-hydroxybutyryl] kanamycin A. Synthetic Pathway: kanamycin A first reacted with N- (benzyloxycarbonyloxy) -succinimide to generate 6’-N-benzyloxycarbonyl kanamycin A, which reacted with equimolar L (-) - 4-benzyloxycarbonylamino-2-hydroxybutyric acid N-hydroxy succinimide ester condensation, the hydrogenolysis to remove the protective group that Ⅰ Ⅰ oxidized by periodic acid to produce 1-NL (-) - 4-amino 2-hydroxybutyryl-2-deoxystreptamine. The Schiff base formed by the reaction of Ⅰ with p-methoxybenzaldehyde was reduced and formed by NaBH 4 reduction 3-N-p-methoxybenzyl-2-deoxystreptamine, the same two degradation products as the corresponding products from butirosin A, demonstrating that L (-) - 4-amino-