Theoretical modeling of the nonenzymatic solvolysis of CMP-NeuAc in an acidic environment

Bartosz Trzaskowski, Andrzej Leś, Abraham F. Jalbout, Ludwik Adamowicz, Per E M Siegbahn

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A density-functional-theory investigation of the nonenzymatic solvolysis of the cytydine 5′-monophosphate N-acetylneuraminic acid and its derivatives in the acidic environment is presented. The theoretical calculations of the second stage of the reaction mechanism are in agreement with the hypothesis of a dissociative oxocarbenium-like transition state with proton transfer as a key part of the reaction. The geometries of the transition states of the reactions yielding α-methyl and β-methyl glycosides are essentially different. This study provides new theoretical data that can be helpful in elucidating the mechanism of the carbohydrates hydrolysis as well as other reactions catalyzed by the glycosyltransferases.

Original languageEnglish (US)
Pages (from-to)90-97
Number of pages8
JournalJournal of Molecular Structure: THEOCHEM
Volume820
Issue number1-3
DOIs
StatePublished - Oct 15 2007

Fingerprint

solvolysis
Cytidine Monophosphate
Glycosides
Glycosyltransferases
Proton transfer
N-Acetylneuraminic Acid
Carbohydrates
Density functional theory
Protons
Hydrolysis
Derivatives
Acids
Geometry
glucosides
carbohydrates
hydrolysis
density functional theory
acids
protons
geometry

Keywords

  • CMP-NeuAc
  • DFT
  • Sialic acid
  • Sialyltransferase
  • Solvolysis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

Theoretical modeling of the nonenzymatic solvolysis of CMP-NeuAc in an acidic environment. / Trzaskowski, Bartosz; Leś, Andrzej; Jalbout, Abraham F.; Adamowicz, Ludwik; Siegbahn, Per E M.

In: Journal of Molecular Structure: THEOCHEM, Vol. 820, No. 1-3, 15.10.2007, p. 90-97.

Research output: Contribution to journalArticle

Trzaskowski, Bartosz ; Leś, Andrzej ; Jalbout, Abraham F. ; Adamowicz, Ludwik ; Siegbahn, Per E M. / Theoretical modeling of the nonenzymatic solvolysis of CMP-NeuAc in an acidic environment. In: Journal of Molecular Structure: THEOCHEM. 2007 ; Vol. 820, No. 1-3. pp. 90-97.
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