New syntheses of 1D- and 1L-1,2-anhydro-myo-inositol and assessment of their glycosidase inhibitory activities.
The 1D and 1L enantiomers of 1,2-anhydro-myo-inositol (conduritol B epoxide) were synthesised from 1D-pinitol and 1L-quebrachitol, respectively, and their activities were compared in selected glycosidase inhibition assays. The 1D enantiomer was found to be the active isomer, functioning as an irreversible inhibitor of sweet almond beta-D-glucosidase. Neither isomer was active against the alpha-D-glucosidase from Bacillus stearothermophilus or the beta-D-galactosidase from Aspergillus oryzae.
Falshaw
A
A
Industrial Research Ltd., Lower Hutt, New Zealand.
Hart
J B
JB
Tyler
P C
PC
D001236:Aspergillus oryzae / Q000201:enzymology; D001426:Bacterial Proteins / Q000037:antagonists & inhibitors; D002236:Carbohydrate Conformation; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D005656:Fungal Proteins / Q000037:antagonists & inhibitors; D001411:Geobacillus stearothermophilus / Q000201:enzymology; D065089:Glycoside Hydrolase Inhibitors; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D007212:Indolizines / Q000494:pharmacology; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D010940:Plant Proteins / Q000037:antagonists & inhibitors; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013379:Substrate Specificity; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors; D001617:beta-Glucosidase / Q000037:antagonists & inhibitors; D054836:Indolizidines
D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; D005656:Fungal Proteins; D065089:Glycoside Hydrolase Inhibitors; D006026:Glycoside Hydrolases; D007212:Indolizines; D007294:Inositol; D010940:Plant Proteins; D001616:beta-Galactosidase; D001617:beta-Glucosidase; C021730:pinitol; C056476:quebrachitol; C011423:conduritol epoxide; C037806:castanospermine; D054836:Indolizidines