Issue 2, 2010

Synthesis and glycosidase inhibitory activity of noeurostegine—a new and potent inhibitor of β-glucoside hydrolases

Abstract

A new, stable hemi-aminal nor-tropane christened noeurostegine was synthesised in 22 steps from levoglucosan and tested for inhibitory activity against glycoside hydrolases. Sweet almond and Thermotoga maritimaβ-glucosidases, coffee bean α-galactosidase, and Asp. oryzaeβ-galactosidase were inhibited in the low micromolar region but significant tightening of binding to Ki 50 nM for almond β-glucosidase was found to occur after pre-incubation. Yeast α-glucosidase and E. coliβ-galactosidase were not inhibited at 1 mM.

Graphical abstract: Synthesis and glycosidase inhibitory activity of noeurostegine—a new and potent inhibitor of β-glucoside hydrolases

Supplementary files

Article information

Article type
Paper
Submitted
08 Sep 2009
Accepted
19 Oct 2009
First published
23 Nov 2009

Org. Biomol. Chem., 2010,8, 433-441

Synthesis and glycosidase inhibitory activity of noeurostegine—a new and potent inhibitor of β-glucoside hydrolases

T. S. Rasmussen and H. H. Jensen, Org. Biomol. Chem., 2010, 8, 433 DOI: 10.1039/B918576C

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