Modification of glycopeptide antibiotic eremomycin by the action of alkyl halides and study on antibacterial activity of the compounds obtained.
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.
Pavlov
A Y
AY
Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow.
Olsufyeva
E N
EN
Berdnikova
T F
TF
Malkova
I V
IV
Preobrazhenskaya
M N
MN
Risbridger
G D
GD
D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006020:Glycopeptides; D006094:Gram-Positive Bacteria / Q000187:drug effects*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D006020:Glycopeptides; D006846:Hydrocarbons, Halogenated; C053759:eremomycin