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 irreve...

Full description

Saved in:
Bibliographic Details
Published in:Carbohydrate research 2000-11, Vol.329 (2), p.301-308
Main Authors: Falshaw, A, Hart, J B, Tyler, P C
Format: Article
Language:English
Subjects:
Aspergillus oryzae - enzymology
Bacterial Proteins - antagonists & inhibitors
beta-Galactosidase - antagonists & inhibitors
beta-Glucosidase - antagonists & inhibitors
Carbohydrate Conformation
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - pharmacology
Fungal Proteins - antagonists & inhibitors
Geobacillus stearothermophilus - enzymology
Glycoside Hydrolase Inhibitors
Glycoside Hydrolases - antagonists & inhibitors
Indolizines - pharmacology
Inositol - analogs & derivatives
Inositol - chemical synthesis
Inositol - chemistry
Inositol - pharmacology
Magnetic Resonance Spectroscopy
Plant Proteins - antagonists & inhibitors
Stereoisomerism
Structure-Activity Relationship
Substrate Specificity
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0008-6215
DOI:10.1016/S0008-6215(00)00192-0