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Updated: Aug 26, 2026

Structural Biology and Analytical Chemistry Approaches for Characterizing C-Glycoside Metabolic Enzymes in Human Gut Microbiota
Published on: May 23, 2025
Hydrolysis of alpha- and beta-glycosides. New experimental data and modeling of reaction pathways
Pierre Deslongchamps1, Shigui Li, Yves L Dory
1Département de Chimie, Institut de Pharmacologie, Université de Sherbooke, 3001, 12e Avenue Nord, Sherbrooke, Québec J1H 5N4, Canada. pierre.deslongchamps@usherbrooke.ca
Abstract:
[reaction: see text] The cyclization of oxocarbenium ion conformers 6alpha and 6beta (from 11E and 11Z) gave only the beta-glycoside 1beta, and the addition of methanol to the oxocarbenium ion 3 yielded mainly the alpha-glycoside 1alpha with both experiments being carried out under kinetically controlled conditions. RHF/6.31G calculations reproduce well these experimental results and show that the endocyclic and the exocyclic C-O bond cleavage processes can compete in the hydrolysis of 1beta, whereas 1alpha gets hydrolyzed by exocyclic C-O bond cleavage only.
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