AN UNEXPECTED INTRAMOLECULAR CYCLIZATION OF ISOTHIOURONIUM TEICOPLANINS: II. REACTION MECHANISM AND BIOLOGICAL ACTIVITY

N15-Isothiouronium derivatives of teicoplanin and its aglycone submitted to alkaline condition give rise to an intramolecular cyclization. The structures of the new γ-lactam derivatives were determined by using 1H NMR, IR and fast atom bombardment mass spectra. The cyclization mechanism was interpre...

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Bibliographic Details
Published in:Journal of antibiotics 1989/08/25, Vol.42(8), pp.1276-1282
Main Authors: TRANI, ALDO, FERRARI, PIETRO, PALLANZA, ROSETTA, CIABATTI, ROMEO
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Cyclization
Glycopeptides - chemical synthesis
Glycopeptides - pharmacology
Guanidines - chemical synthesis
Isothiuronium - analogs & derivatives
Lactams - chemical synthesis
Lactams - pharmacology
Microbial Sensitivity Tests
Molecular Structure
Spectrum Analysis
Teicoplanin
Thiourea - analogs & derivatives
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Summary:N15-Isothiouronium derivatives of teicoplanin and its aglycone submitted to alkaline condition give rise to an intramolecular cyclization. The structures of the new γ-lactam derivatives were determined by using 1H NMR, IR and fast atom bombardment mass spectra. The cyclization mechanism was interpreted on the basis of the identification of the intermediate structure. The poor in vitro antibacterial activity of the new cyclic compounds and the negligible affinity for the synthetic peptidoglycan model Ac2-L-Lys-D-Ala-D-Ala is probably due to the lack of the N-17 amidic proton and to the lack of the basic character of the nitrogen in position 15.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.42.1276