Synthesis and biological activity of N63-carboxypeptides of teicoplanin and teicoplanin aglycone.
A series of peptide derivatives of teicoplanin A2 (CTA) and deglucoteicoplanin (TD) was prepared by condensation of the 63-carboxyl function with the alpha-amino group of selected amino acids and their derivatives. The modification of the ionic character of CTA and TD influenced their in vitro and in vivo antimicrobial properties to a different extent, depending on the structure of the amino acidic moiety at C-63. A certain effect on binding strength to Ac2-L-Lys-D-Ala-D-Ala, a synthetic model of the antibiotic's target peptide, was also observed.
Malabarba
A
A
Merrell Dow Research Institute, Lepetit Research Center, Varese, Italy.
Ferrari
P
P
Cietto
G
G
Pallanza
R
R
Berti
M
M
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D006020:Glycopeptides / Q000138:chemical synthesis / Q000627:therapeutic use; D006094:Gram-Positive Bacteria / Q000187:drug effects; D051379:Mice; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000494:pharmacology; D018805:Sepsis / Q000188:drug therapy; D013290:Streptococcal Infections / Q000188:drug therapy; D013329:Structure-Activity Relationship; D017334:Teicoplanin / Q000031:analogs & derivatives
D000900:Anti-Bacterial Agents; D006020:Glycopeptides; D010456:Peptides, Cyclic; D017334:Teicoplanin; C063101:teicoplanin aglycone