82 Trestatin A,B,Cの構造

概要

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Trestatins A, B and C which were isolated from the culture filtrate of Streptomyces dimorphogenes NR-320-OM7HB are new amino-oligosaccharides possessing potent inhibitory activity against various α-amylases. Their structures have been determined by chemical degradation and spectral studies. Trestatins A (C_<56>H_<94>N_2O_<40>), B (C_<37>H_<63>NO_<28>) and C (C_<75>H_<125>N_3O_<52>) are water-soluble, basic substances of homologous nature. Upon acid hydrolysis, Trestatins A, B and C gave D-glucose and a tricyclic oxazolidine (1) derived from 3 in common. This finding coupled with titration, MW and PMR data revealed the components (Table 2) of each Trestatin. In order to determine the sequences, each Trestatin was subjected to mild acid hydrolysis which also gave D-glucose, trehalose, maltose, glucotriose (4) and glucotetraose (5) in common. The linkage between 3 and 5 was elucidated on the basis of T_1 data, which revealed the structure of Trestatin B. From the hydrolyzate of Trestatin A, basic fragments such as 13, 14, 15, 16, 17 and 18 were obtained. In case of Trestatin C, fragments 17 and 19 were obtained in addition to 13-16. Their structures were clarified mainly by PMR and CMR, which in turn led to revealing the structures of Trestatins A and C.
天然有機化合物討論会の論文
1980-09-10