An exploratory conformational analysis of D and L β-6-deoxyglucose. An ab initio and DFT approach

Gabrille F.C. Yeung, David H. Setiadi, Gregory A. Chass, Imre G. Csizmadia

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

6-Deoxyglucose is not only a model compound for glucose, but it is also a hexokinase inhibitor. The molecule may be 1C4 and 4C1 ring structures. It occurs on α and β isomers, each having assigned 81 MDCA-predicted nomenclature to the conformations. An exploratory ab initio conformational analysis was undertaken on β-6-deoxyglucose at each of the RHF/3-21G, RHF/6-31G(d) and B3LYP/6031G(d) levels of theory. Apart from the anomeric hydroxyl group, there are four C-OH rotamers. Full conformational analysis will reveal the global minima of D- and L-β-6-deoxyglucose. Calculations revealed both D and L of 1C4 and 4C1 conformers to have the lowest energy conformation. It was found that the molecule was greatly stabilized by multiple hydrogen bonds. These hydrogen bonds took several forms; unidirect or non-unidirect clockwise and anti-clockwise hydrogen bonding or tunneling motion, which is dependent on the chair configurations. These stable conformations may suggest the effectiveness of this inhibitor and structural mechanisms in forming polymers.

Original languageEnglish
Pages (from-to)393-396
Number of pages4
JournalJournal of Molecular Structure: THEOCHEM
Volume666-667
DOIs
Publication statusPublished - Dec 29 2003

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Keywords

  • 6-Deoxyglucose
  • Ab initio
  • Conformational analysis
  • DFT
  • Hydrogen bonding
  • Tunneling motion

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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