A free-energy relationship between the rate of acidic hydrolysis of glycosides and the pKa of isofagomines

Mahmoud M. Al-Ktaifani, Daniel P. Chapman, Matthew D. Francis, Peter B. Hitchcock, John F. Nixon, László Nyulászi

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

A new answer to a 100-year-old puzzle is presented here, namely, why are galactosides hydrolyzed faster than glucosides? This disparity was long attributed to facilitation by axial OH groups of a conformational change en route to the transition state. However, the results presented here indicate that differences in the electron-withdrawing effects (represented by arrows) of equatorial (A) and axial OH groups (B) are decisive.

Original languageEnglish
Pages (from-to)3447-3449
Number of pages3
JournalAngewandte Chemie - International Edition
Volume40
Issue number18
DOIs
Publication statusPublished - Sep 17 2001

Keywords

  • Amines
  • Basicity
  • Glycosides
  • Hydrolysis
  • Kinetics

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'A free-energy relationship between the rate of acidic hydrolysis of glycosides and the pK<sub>a</sub> of isofagomines'. Together they form a unique fingerprint.

  • Cite this