TEICOPLANIN, ANTIBIOTICS FROM ACTINOPLANES TEICHOMYCETICUS NOV. SP: VII. PREPARATION AND NMR CHARACTERISTICS OF THE AGLYCONE OF TEICOPLANIN

Several hydrolytic reactions that transform teicoplanin or its pseudo-aglycones into the aglycone with good yields are described. The most interesting approach is hydrolytic removal of the sugars in benzyl alcohol with the formation of the aglycone benzyl ester which is then submitted to hydrogenoly...

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Bibliographic Details
Published in:Journal of antibiotics 1986, Vol.39(10), pp.1430-1442
Main Authors: MALABARBA, ADRIANO, FERRARI, PIETRO, GALLO, GIAN GUALBERTO, KETTENRING, JURGEN, CAVALLERI, BRUNO
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Biological and medical sciences
Chemical Phenomena
Chemistry
General pharmacology
Glycopeptides - chemical synthesis
Magnetic Resonance Spectroscopy
Medical sciences
Pharmacology. Drug treatments
Physicochemical properties. Structure-activity relationships
Teicoplanin
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Summary:Several hydrolytic reactions that transform teicoplanin or its pseudo-aglycones into the aglycone with good yields are described. The most interesting approach is hydrolytic removal of the sugars in benzyl alcohol with the formation of the aglycone benzyl ester which is then submitted to hydrogenolysis. A detailed description of the 1H and 13C NMR spectra of the teicoplanin aglycone hydrochloride is presented. All the signals were attributed to the hydrogen and carbon atoms using homo and heteronuclear COSY. The relevant interactions through space between the hydrogen atoms were obtained by NOE. The structural aspects are discussed in terms of the well-known mechanism of action of the glycopeptide antibiotics.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.39.1430