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.
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Cardona, F., Goti, A., Picasso, S., Vogel, P., & Brandi, A. (2000). Polyhydroxypyrrolidine glycosidase inhibitors related to (+)-lentiginosine. Journal of Carbohydrate Chemistry, 19(4-5), 585–601. https://doi.org/10.1080/07328300008544101
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2000
19
4-5
585
601
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.
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