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 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.