Synthesis and glycosidase inhibitory activity of noeurostegine-a new and potent inhibitor of beta-glucoside hydrolases.
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 maritimabeta-glucosidases, coffee bean alpha-galactosidase, and Asp. oryzaebeta-galactosidase were inhibited in the low micromolar region but significant tightening of binding to K(i) 50 nM for almond beta-glucosidase was found to occur after pre-incubation. Yeast alpha-glucosidase and E. colibeta-galactosidase were not inhibited at 1 mM.
Rasmussen
Tina Secher
TS
Department of Chemistry, Aarhus University, Langelandsgade 140, DK-8000, Aarhus C, Denmark.
Jensen
Henrik Helligsø
HH
D020134:Catalytic Domain; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D005030:Ethylenes / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D009662:Nortropanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012991:Solanaceous Alkaloids / Q000737:chemistry / Q000494:pharmacology; D020124:Thermotoga maritima / Q000201:enzymology
D004791:Enzyme Inhibitors; D005030:Ethylenes; D009662:Nortropanes; D012991:Solanaceous Alkaloids; C547946:noeurostegine; C095613:calystegine B(2); C036216:ethylene; D006026:Glycoside Hydrolases