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

Tina Secher Rasmussen; Henrik Helligsø Jensen

doi:10.1039/B918576C

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Organic & Biomolecular Chemistry

Issue 2, 2010

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

Tina Secher Rasmussen and Henrik Helligsø Jensen

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

DOI: 10.1039/B918576C
Received 08 Sep 2009, Accepted 19 Oct 2009
First published on the web 23 Nov 2009

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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 K_i 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.

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Experimental section, NMR spectra, and Michaelis–Menten and Hanes plots
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Organic & Biomolecular Chemistry

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

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