Novel analogues of anthracycline antibiotics containing 2,3,6-tride-oxy-3-amino-3-C-methyl-L-arabino-hexose (L-eremosamine)
E. N. Olsufyeva, L. V. Bakinowsky, M. N. Preobrazhenskaya, E. De Clerq, J. Balzarini
Institute of New Antibiotics, Academy of Medical Sciences of the USSR, Moscow, N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow; Rega Institute for Medical Research, Katholieke Universiteit, Leuven, B-3000 Leuven, Belgium
Abstract: The interaction of 1,4-di-O-acetyl-N-trifluoroacetyl-L-eremosamine (α:β 1:2 or 1:4) with ε-rhodomycinone, carminomycinone or 14-O-acetyloxycarminomycinone in the presence of trimethylsilyltriflate afforded the corresponding 4-O-acetyl-N-trifluoroacetyl-L-eremosaminides. L-Eremosamine (4-epi-L-vancosamine) was obtained by hydrolysis of the glycopeptide antibiotic eremomycine. Deblocking of the ε-rhodomycinone and carminomycinone glycosides led to the O,N-unprotected α-L-glycosides. Cytostatic properties of the new anthracyclinone glycosides were investigated.
Russian Journal of Bioorganic Chemistry 1991, 17 (4):548-555