An exploratory conformational analysis of d and l β-6-deoxyglucose. An ab initio and DFT approach

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.