SPATIAL CONFIGURATION OF CARBOHYDRATE PART OF CARMINOMYCIN-II AND CARMINOMYCIN-III

  • 1 January 1982
    • journal article
    • research article
    • Vol. 27  (4) , 258-263
Abstract
A neutral fragment of the carbohydrate part of the molecule was isolated in the form of a cyclic acetal (3,5-dinitrobenzoate) from carminomycins II and III, belonging to the anthracyclines. The acetal preserved all asymmetric centers. Methanolysis of the cyclic acetal resulted in formation of the aldol dimethyl acetal and propylene glycol (3,5-dinitrobenzoate) with isolated asymmetric centers. On the basis of the optic and spectral properties of these compounds it was found that carminomycins II and III differed in the configuration of 2 asymmetric C atoms, i.e, acetal atom and the atom in propylene glycol. They had configurations of R (-) in carminomycin II and S (+) in carminomycin III. The third asymmetric center of the acetal in both antibiotics was the same, i.e., S (+).

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