Synthesis and biological activity of derivatives of glycopeptide antibiotics eremomycin and vancomycin nitrosated, acylated or carbamoylated at the N-terminal.
Nitrosation, carbamoylation or acylation of the glycopeptide antibiotics eremomycin or vancomycin produced series of derivatives substituted at the N-terminus of the peptides. Though the modified amino group in these derivatives is not capable of protonation, N-nitroso derivatives retain antibacterial activity in vitro and in vivo. N-Carbamoyleremomycin has low activity, and N-Cbz-eremomycin and N-Boc-eremomycin are devoid of antibacterial activity, both in vitro and in vivo.
Pavlov
A Y
AY
Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow.
Berdnikova
T F
TF
Olsufyeva
E N
EN
Lazhko
E I
EI
Malkova
I V
IV
Preobrazhenskaya
M N
MN
Testa
R T
RT
Petersen
P J
PJ
D000595:Amino Acid Sequence; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002240:Carbohydrate Sequence; D006020:Glycopeptides; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D013203:Staphylococcal Infections / Q000188:drug therapy; D013329:Structure-Activity Relationship; D014640:Vancomycin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D006020:Glycopeptides; C053759:eremomycin; D014640:Vancomycin