C-5a-substituted validamine type glycosidase inhibitors. (22nd February 2017)

• Record Type: Journal Article
• Authors: Schalli, Michael; Wolfsgruber, Andreas; Gonzalez Santana, Andres; Tysoe, Christina; Fischer, Roland; Stütz, Arnold E.; Thonhofer, Martin; Withers, Stephen G.
• Is Part Of: Carbohydrate research. Volume 442(2017)
• Page Start: 1
• Page End: 9
• Publication Date: 2017-02-22
• Subjects: Aminocyclitol -- Carbasugar -- Glycosidase inhibitor; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2017.01.006
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: A series of N -alkyl derivatives of the D-galactosidase inhibitor 1, 4-di- epi -validamine featuring lipophilic substituents at position C-5a was prepared and screened for their glycosidase inhibitory properties. Products turned out selective for β-galactosidases as well as β-glucosidases. Graphical abstract: Highlights: A simple route enables access to C-5a-hydroxylated derivatives of 1, 4-di- epi -validamine. Regioselective derivatization with a range of isocyanates provides one-step access to lipophilic analogs. Additional modifications are available by simple 1- N -alkylation. Final products are inhibitors of β-galactosidases.