47 塩基性マクロライドの構造解析における化学イオン化マススペクトロメトリーの利用

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It is well known that chemical ionization mass spectrometry (CIMS) is more useful for molecular weight determination and structural analysis of relatively non-volatile compounds than conventional electron impact mass spectrometry (EIMS). Therefore we attempt to apply this method to the structural characterization of basic macrolide antibiotics, which contain large lactone ring and sugar moieties. As the basic investigation, CI mass spectra of several known 16-membered basic macrolides were examined using isobutane, ammonia and ammonia-d_3 as reagent gas and the following results were obtained. 1. CI(i-C_4H_<10>, NH_3) mass spectra of the above compounds show protonated molecular ion(MH^+) as base peak, which indicate correctly molecular weight. 2. As the major fragment ions, two species, aglycone- and sugar-derived ions, are mainly arise from the cleavage of glycosidic bond. 3. As to the sugar-derived ions, there is a great difference between amino sugar and neutral sugar. Namely, three amino sugar-derived ions which are produced by both side cleavage on the glycosidic bond are found in all cases, while, concerning the neutral sugar, the oxonium type ions obtained by oneside cleavage of glycosidic bond in macrolide molecule is only observed. 4. The structures of these ions are estimated by the shifting technique (NH_3→ND_3). Finally, we apply the mentioned above results to the structural analysis of the five new basic macrolide antibiotics, Mycinamicin produced by micromonospora sp. A-11725.
天然有機化合物討論会の論文
1979-09-20

47 塩基性マクロライドの構造解析における化学イオン化マススペクトロメトリーの利用

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