[Antibiotic N',N''-dibenzyleremomycin with reduced 1,2-peptide bond].
Eremomycin derivatives with benzylated amino groups of both residues of eremosamine and with (R) or (S)-2-amino-4-methylpentyl substituted for N-methyl-D-Leu, the first amino acid residue of its heptapeptide, were synthesized to study the role of the peptide bond between the first and the second amino acid residues of the heptapeptide moiety of the antibiotic in its interaction with the precursors of the bacterial cell wall peptidoglycan and exhibition of its antibacterial activity. Comparison of the antibacterial activities of N',N"-dibenzyleremomycin, de-(N-methyl-D-Leu)-N',N"-dibenzyleremomycin, and its N-(2-amino-4-methylpentyl)-derivative (1,2-deoxo-N',N"-dibenzyleremomycin) demonstrated that cleavage or replacement of the first amino acid residue by the corresponding aminoalkyl residue results in a decrease in its antibacterial activity towards both vancomycin-sensitive and vancomycin-resistant strains of microorganisms. The English version of the paper.
Printsevskaia
S S
SS
Institute of New Antibiotics, Russian Academy of Medical Sciences, ul. Bol'shaya Pirogovskaya 11, Moscow, 119867 Russia.
Olsuf'eva
E N
EN
Lazhko
E I
EI
Preobrazhenskaia
M N
MN
D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology*; D006020:Glycopeptides; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D010455:Peptides / Q000737:chemistry; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D006020:Glycopeptides; C460041:N',N''-dibenzyleremomycin; D010455:Peptides; C053759:eremomycin