Antibiotic substances produced by Pseudomonas aeruginosa; syntheses of Pyo Ib, Pyo Ic, and Pyo III.
Antibiotic substances produced by Pseudomonas aeruginosa; syntheses of Pyo Ib, Pyo Ic, and Pyo III.
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DOI：
10.1016/s0021-9258(18)55737-9
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发表时间：
1952-05
期刊：
影响因子：
--
通讯作者：
I. Wells
中科院分区：
文献类型：
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作者：
I. Wells
Hays等人(1)于1945年报道从铜绿假单胞菌培养物中分离出五种结构未知的抗生素物质。这些化合物不溶于水，但可溶于多种有机溶剂。从光谱上看，它们密切相关，尽管它们针对合适的测试微生物的抗生素活性差异很大。由于缺乏更好的命名法，这些物质按照分离的顺序被命名为 Pyo Ib、Pyo Ic、Pyo II、Pyo III 和 Pyo IV。 由于铜绿假单胞菌提取物已成功用于治疗某些细菌感染 (I)，因此认为必须从结构上鉴定这些分离的抗生素物质。最成功的降解方法是臭氧化 (2)。通过该程序，Pyo III每摩尔产生1摩尔正辛醛，并且Pyo Ic每摩尔产生1摩尔N-辛基邻氨基苯甲酸。后一个片段约占 Pyo Ic (1) 测定分子量的一半。因为这些是唯一分离的结构上重要的片段，所以很难就 Pyo III 和 Pyo Ic 的整体结构得出任何结论。当注意到 2-甲基-4-羟基喹啉 (3) 在 95% 乙醇中的紫外吸收光谱与同一溶剂中的 Pyo Ib 和 Pyo Ic 的紫外吸收光谱定性相同时，这一困难得到了部分解决。对这种化合物进行的研究表明，(a) 在还原 Adams 氧化铂催化剂存在下，通过在冰醋酸中氢化 2-甲基-羟基喹啉生成的四氢-2-甲基-4-羟基喹啉 1 具有与八氢 Pyo Ib 和八氢 Pyo Ic (l) 定性相同的紫外吸收光谱，以及 (b) 2-甲基-4-羟基喹啉的臭氧化产生了一个片段，经光谱鉴定为N-乙酰邻氨基苯甲酸。 1 然而，这些发现令人困惑，因为与 2-甲基-4-羟基喹啉类比，Pyo Ic 应该是 2-壬基-4-羟基喹啉，而确定的分子
The isolation of five antibiotic substances of unknown structure from cultures of Pseudomonas aeruginosa was reported by Hays et al.(1) in 1945. These compounds were insoluble in water but were soluble in a wide variety of organic solvents. Spectroscopically, they were closely related, although their antibiotic activities against a suitable test organism varied considerably. For lack of better nomenclature, these substances were named, in the order of their isolation, Pyo Ib, Pyo Ic, Pyo II, Pyo III, and Pyo IV.Since extracts of P. aeruginosa had been used successfully in the treatment of certain bacterial infections (I), it was deemed essential that these isolated antibiotic substances be identified structurally. The most successful method of degradation was ozonization (2). By this procedure, Pyo III yielded 1 mole of n-octanal per mole, and Pyo Ic yielded 1 mole of N-caprylanthranilic acid per mole. The latter fragment represented about one-half of the determined molecular weight of Pyo Ic (1). Because these were the only structurally significant fragments isolated, it was difficult to reach any conclusions concerning the over-all structures of Pyo III and Pyo Ic. This difficulty was partially resolved when it was noted that the ultraviolet absorption spectrum of 2-methyl-4-quinolinol (3) in 95 per cent ethanol was qualitatively the same as those of Pyo Ib and Pyo Ic in the same solvent. Investigations carried out with this compound revealed (a) that tetrahydro-2-methyl-4quinolino1, produced by hydrogenating 2-methyll-quinolinol in glacial acetic acid in the presence of reduced Adams’ platinum oxide catalyst, possessed qualitatively the same ultraviolet absorption spectrum as octahydro Pyo Ib and octahydro Pyo Ic (l), and (b) that ozonization of 2-methyl-4-quinolinol produced a fragment spectroscopically identified as N-acetylanthranilic acid. 1 However, these findings were confusing, since, by analogy to 2-methyl-4-quinolinol, Pyo Ic ought to be 2-nonyl-4-quinolinol, whereas the determined molecular