Acidity Constants of the Tetracycline Antibiotics

Acidity Constants of the Tetracycline Antibiotics
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DOI:
10.1021/ja01597a081
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发表时间:
1956-08
影响因子:
15
通讯作者:
C. R. Stephens;K. Murai;K. J. Brunings;R. Woodward
C. R. Stephens;K. Murai;K. J. Brunings;R. Woodward
中科院分区:
化学1区
文献类型:
--
作者:
C. R. Stephens;K. Murai;K. J. Brunings;R. Woodward

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三个观察到的抗生素土霉素,金霉素和四环素的解离常数已被分配到特定的酸性基团。在每种情况下,第一次解离是由于环A中的三羰基系统,第二次解离是由于二甲基铵官能团1,第三次解离是由于酚性β-二酮系统(C)。10,C. ll,C. 12)。结果表明,在中性溶液中,这些抗生素主要以两性离子形式存在。
The three observed dissociation constants of the antibiotics oxytetracycline, chlorotetracycline and tetracycline have been assigned to specific acidic groupings. In each case, the first dissociation is due to the tricarbonyl system in ring A, the second to the dimethylammonium function1 and the third to the phenolic ß-diketone system (C. 10, C. ll, C. 12). The findings reveal that in neutral solution these antibiotics exist largely as zwitterions.