A series of 13 aminocyclitol derivatives belonging to two different families is described. Their configuration is governed by the regio- and stereocontrolled epoxide opening of a suitably protected conduritol-B epoxide. Studies on several glycosyl processing enzymes indicate that some of them are good inhibitors of glucosylceramide hydrolase. A rationale to account for preliminary structure-activity relationships is provided.
Research Unit on Bioactive Molecules (RUBAM), Department de Química Orgànica Biológica, Institut d'Investigaciones Quimiques i Ambientals de Barcelona (IIQAB-C.S.I.C), Jordi Girona 18-26, 08034, Barcelona, Spain.
