31 塩基性配糖体抗生物質Aculeximycinの構造研究(口頭発表の部)

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Aculeximycin (ACM) was isolated from a culture of Streptosporangium albidum, which exhibits an inhibitory against Gram-positive bacteria, fungi and yeast. It also shows a potent uncoupler of oxidative phosphorylation with rat-liver mitochondria. N-Diacetyl derivative (2) of ACM was degraded by the following sequence, 1) DBU-MeOH, 2) O_3 / NaBH_3CN and 3) NaIO_4/NaBH_4. Treatment of 2 with 5% DBU-MeOH gave an N-Ac-aculexitriose (3) and an epimeric pair of counterparts named N-Ac-pseudoaglycones I (4) and II (5). Ozonolysis of 4 followed by reduction with NaBH_3CN yielded three components, AOP-I (6), AOP-IIs (7) and AOP-IIIs (8). Further oxidation of 8 with NaIO_4, followed by NaBH4 reduction afforded APP-I (12) and APP-II (13). The structures of these degradation products and their derivatives have been determined by spectroscopic analyses. The relative and absolute configurations of them were tried to determine by NOE, Rychnovsky's, advanced Mosher's and/or exciton chirality methods. The structures of 8 were established by deuterium labeled experiment and preparation of partial periodate oxidative products, APP-I+C1 and DM APP-II+C2. A construction of 6, 7 and 8 moieties leading to 4 was accomplished by application of HMBC and HOHAHA to 4. The location of the remaining glycosidic linkage proved to be at C-11 in consideration of a mechanism of a specific glycosidic bond cleavage with DBU and the resulting epimeric mixture of 4 and 5. Finally, the total structure of ACM can be proposed as shown in Fig. 1.
天然有機化合物討論会の論文
1992-09-10

31 塩基性配糖体抗生物質Aculeximycinの構造研究(口頭発表の部)

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