N15-ALKYL AND N15, N15-DIALKYL DERIVATIVES OF TEICOPLANIN ANTIBIOTICS

The synthesis and the biological properties of a series of N15-alkyl and N15, N15-dialkyl derivatives of teicoplanin A2, its pseudoaglycones and aglycone are described. The alkylation of the terminal amino group did not affect the ability of these teicoplanin derivatives to bind with Ac2-L-Lys-D-Ala...

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Bibliographic Details
Published in:Journal of antibiotics 1990/09/25, Vol.43(9), pp.1107-1121
Main Authors: MALABARBA, ADRIANO, TRANI, ALDO, KETTENRING, JÜRGEN, GERLI, ERMINIO, PALLANZA, ROSA, BERTI, MARISA, CAVALLERI, BRUNO
Format: Article
Language:English
Subjects:
Alkylation
Amino Acid Sequence
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - metabolism
Anti-Bacterial Agents - pharmacology
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Bacteria - drug effects
Biological and medical sciences
Chromatography, High Pressure Liquid
Glycopeptides - chemistry
Glycopeptides - metabolism
Glycopeptides - pharmacology
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Medical sciences
Molecular Sequence Data
Molecular Structure
Peptides - metabolism
Pharmacology. Drug treatments
Sepsis - drug therapy
Streptococcal Infections - drug therapy
Streptococcus pyogenes - drug effects
Teicoplanin
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Summary:The synthesis and the biological properties of a series of N15-alkyl and N15, N15-dialkyl derivatives of teicoplanin A2, its pseudoaglycones and aglycone are described. The alkylation of the terminal amino group did not affect the ability of these teicoplanin derivatives to bind with Ac2-L-Lys-D-Ala-D-Ala, a synthetic model of the antibiotic's target peptide in bacterial cell walls, but influenced their in vitro and in vivo antimicrobial activities to a different extent, depending on the structure and length of the alkyl chains and the type and number of sugars present.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.43.1107