Conformational analysis of cellobiose by electronic structure theories

Alfred D. French, Glenn P. Johnson, Christopher J. Cramer, Gábor I. Csonka

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42 Scopus citations

Abstract

Adiabatic φ/ψ maps for cellobiose were prepared with B3LYP density functional theory. A mixed basis set was used for minimization, followed with 6-31+G(d) single-point calculations, with and without SMD continuum solvation. Different arrangements of the exocyclic groups (38 starting geometries) were considered for each φ/ψ point. The vacuum calculations agreed with earlier computational and experimental results on the preferred gas phase conformation (anti-φ H, syn-ψ H), and the results from the solvated calculations were consistent with the (syn φ HH conformations from condensed phases (crystals or solutions). Results from related studies were compared, and there is substantial dependence on the solvation model as well as arrangements of exocyclic groups. New stabilizing interactions were revealed by Atoms-In-Molecules theory.

Original languageEnglish (US)
Pages (from-to)68-76
Number of pages9
JournalCarbohydrate Research
Volume350
DOIs
StatePublished - Mar 1 2012

Keywords

  • Aqueous solvation
  • Carbohydrate
  • Cellulose
  • Conformational analysis
  • Disaccharide
  • Mapping

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