MODIFICATION OF GLYCOPEPTIDE ANTIBIOTIC EREMOMYCIN BY THE ACTION OF ALKYL HALIDES AND STUDY ON ANTIBACTERIAL ACTIVITY OF THE COMPOUNDS OBTAINED

• Published in: Journal of antibiotics 1994/02/25, Vol.47(2), pp.225-232
• Main Authors: PAVLOV, A. Y., OLSUFYEVA, E. N., BERDNIKOVA, T. F., MALKOVA, I. V., PREOBRAZHENSKAYA, M. N., RISBRIDGER, G. D.
• Format: Article
• Language: English
• Subjects: Amino Acid Sequence; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Glycopeptides; Gram-Positive Bacteria - drug effects; Hydrocarbons, Halogenated - chemical synthesis; Hydrocarbons, Halogenated - chemistry; Hydrocarbons, Halogenated - pharmacology; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Molecular Sequence Data; Spectrometry, Mass, Fast Atom Bombardment; Structure-Activity Relationship
• ISSN: 0021-8820; 1881-1469
• DOI: 10.7164/antibiotics.47.225

Alkylation of glycopeptide antibiotic eremomycin by the action of different alkyl halides leads, depending on the structure of alkyl halides used, to eremomycin derivatives of six types; alkylated at the N-terminus, quaternary compounds at the N-terminus, eremomycin esters, esters of eremocycin alkylated at the N-terminus, esters of eremomycin quaternised at the N-terminus, esters of eremomycin alkylated both at the N-terminus and at the aminogroup of disaccharide branch. Five compounds demonstrated high antibacterial activity in vitro, N-allyleremomycin and methyl ester of N, N-dimethyleremomycin being at least as good as the parent eremomycin.