Spatial configuration of the carbohydrate portion of carminomycins Ii and IIi
Spiridonova, I.A.; Lomakina, N.N.
Antibiotiki 27(4): 258-263
1982
ISSN/ISBN: 0003-5637 PMID: 6284023 Document Number: 195495
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 anthracyclines. The acetal preserved all the asymmetric centers. Methanolysis of the cyclic acetal resulted in formation of 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 carbon 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(+).