Biologically active branched-chain aminocyclopentane tetraols from d-galactose

• Published in: Monatshefte für Chemie Vol. 150; no. 5; pp. 861 - 870
• Main Authors: Schalli, Michael, Weber, Patrick, Nasseri, Seyed A., Gomez, Ana Torvisco, Müller, Philipp, Stütz, Arnold E., Withers, Stephen G., Wolfsgruber, Andreas, Wrodnigg, Tanja M.
• Format: Journal Article
• Language: English
• Published: Vienna Springer Vienna 01.05.2019; Springer Nature; Springer Nature B.V
• Subjects: Analytical Chemistry; Chain branching; Chains; Chemistry; Chemistry and Materials Science; Chemistry, Multidisciplinary; Chemistry/Food Science; Galactose; Galactosidase; Inhibitors; Inorganic Chemistry; Isomers; Organic Chemistry; Original Paper; Physical Chemistry; Physical Sciences; Science & Technology; Stereoselectivity; Theoretical and Computational Chemistry; Carbocycles; Ene reactions; Carbohydrates; Aminoalcohols; Cyclizations; Structure–activity relationships; PHARMACOLOGICAL CHAPERONE THERAPY; LYSOSOMAL BETA-GALACTOSIDASE; STORAGE DISEASES; MUTANT ENZYME; Structure-activity relationships; GLYCOSIDASE INHIBITORS; STRUCTURE VALIDATION; G(M1)-GANGLIOSIDOSIS; MORQUIO-DISEASE; GM1 GANGLIOSIDOSIS; SELECTIVE INHIBITORS
• ISSN: 0026-9247; 1434-4475
• DOI: 10.1007/s00706-019-02428-0

From 1,2;3,4-di- O -isopropylidene- d -galactopyranose, a series of highly functionalized branched-chain cyclopentanes was easily available. The initial partially protected cyclopentane tetraol is a versatile central intermediate and was exploited as subject to various highly regio- and stereoselective structural alterations with a view to prepare selective β- d -galactosidase inhibitors. In line with our findings on recently reported constitutional isomers featuring amino substituents, basic derivatives are medium activity inhibitors of β- d -galactosidases with side activities for β-glucosidases. Graphical abstract