Intramolecular and Water Mediated Tautomerism of Solvated Glycine

J Chem Inf Model. 2024 May 13;64(9):3599-3604. doi: 10.1021/acs.jcim.4c00273. Epub 2024 Apr 15.

Abstract

Understanding tautomerism and characterizing solvent effects on the dynamic processes pose significant challenges. Using enhanced-sampling molecular dynamics based on state-of-the-art deep learning potentials, we investigated the tautomeric equilibria of glycine in water. We observed that the tautomerism between neutral and zwitterionic glycine can occur through both intramolecular and intermolecular proton transfers. The latter proceeds involving a contact anionic-glycine-hydronium ion pair or separate cationic-glycine-hydroxide ion pair. These pathways with comparable barriers contribute almost equally to the reaction flux.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycine* / chemistry
  • Isomerism
  • Molecular Conformation
  • Molecular Dynamics Simulation*
  • Protons
  • Solvents* / chemistry
  • Water* / chemistry

Substances

  • Glycine
  • Water
  • Solvents
  • Protons