CONFORMATIONAL-ANALYSIS OF RANOSYL)-ALPHA-L-LYXO-HEXOPYRANOSYL]ADRIAMICINONE, THE FIRST DOXONTBICIN DISACCHARIDE ANALOG TO BE REPORTED

The solution conformation of ranosyl)-alpha-L-lyxo-hexopyranosyl]adria micinone, the first doxorubicin disaccharide analogue to be reported, has been analysed using nuclear magnetic resonance data and molecular mechanics calculations. In order to consider the possibility of confor mational averaging we have used the NAMFIS programme (NMR analysis of molecular flexibility in solution), that considers all reasonable stru ctures and classifies them with regard to their relative capability of reproducing the experimental data. In this way we have determined the conformation of ring A of the aglycone of the sugar moieties and the preferred orientation around the glycosidic linkages. (C) 1997 Elsevie r Science Ltd.