67 Minosaminomycinの化学的研究

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Minosaminomycin (I, C_<25>H_<46>N_8O_<10>) is an antibiotic isolated from a culture filtrate of a streptomyces related to Actinomyces aureomonopodiales, and inhibits growth of mycobacteria. We report the structure established on the basis of chemical degradations, spectral data and the total synthesis. The acid hydrolysis of I afforded a new aminocyclitol (II), a hydantoin derivative (III) and a degradation product (IV) of kasugamine, together with a trace of leucine, basic amino acids (XII) and a basic glycoside named minobiosamine (V). The absolute structures of II and V were determined to be 1D-1-amino-1-deoxy-myo-inositol (L-myo-inosamine-1) and 1D-1-amino-1-deoxy-4-O-(2,4-diamino-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranosyl)-myo-inositol, respectively, according to their spectral data and optical properties. The syntheses of II and V were successfully carried out from D-inositol and kasuganobiosamine (VI). The structure of III was shown to be a hydantoin derivative consisted of L-leucine and enduracididine (XIIa). By PMR data and determination of C-terminus, the complete structure of I was elucidated as 1D-1-[{1(S)-carboxy-3-methylbutyl}carbamoyl-β-{((4R)-(2-iminoimidazolidinyl)-L alanylamido}]-1-deoxy-4-O-(2,4-diamino-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranosyl)-myo-inositol. The structure was confirmed by the total synthesis.
天然有機化合物討論会の論文
1975-10-01