Synthesis of biotin and fluorescein labeled (–)-lentiginosine.

The important proapoptotic activity of (-)-lentiginosine, the enantiomer of a natural glycosidase inhibitor, associated with its low cytotoxicity, suggests the study of the unknown receptor responsible for the triggering of the proapoptotic cascade. To this purpose derivatives of (-)-lentiginosine 7 and 8, which contain the biotin moiety as an affinity label and fluorescein as fluorophore, have been synthesized. Significantly, the compounds maintain a good activity as the hydroxylentiginosine precursor.