Polyhydroxypyrrolidine glycosidase inhibitors related to (+)-lentiginosine
(+)-Lentiginosine (14) and (7R)-7-hydroxylentiginosine (26), powerful inhibitors of amyloglucosidases, and their enantiomers were obtained in high overall yields by a multistep synthesis involving 1,3-dipolar cycloaddition of enantiopure tartaric acid derived pyrroline N-oxides. Structurally related (S,S)-3,4-dihydroxypyrrolidines 29-33 were synthesized as simpler models and tested towards 24 glycosidases.
Keywords: Aza-c-disaccharides ; alpha-glucosidase inhibitors ; pyrroline n-oxides ; cyclic nitrones ; syncytium formation ; beta-glycosidases ; castanospermine ; cycloaddition ; lentiginosine ; swainsonine
Univ Florence, CNR, Ctr Studio Chim & Strutt Composti Eterociclici &, Dipartimento Chim Organ Ugo Schiff, I-50121 Florence, Italy. Univ Lausanne, BCH, Inst Chim Organ, CH-1015 Lausanne, Switzerland.
Record created on 2005-11-09, modified on 2016-08-08