Ziemniak, Marcin; Pawledzio, Sylwia; Zawadzka-Kazmierczuk, Anna; Dominiak, Paulina M.; Trzybinski, Damian; Kozminski, Wiktor; Zielinski, Rafal; Fokt, Izabela; Priebe, Waldemar; Wozniak, Krzysztof; Pajak, Beata published the artcile< X-ray wavefunction refinement and comprehensive structural studies on bromo-substituted analogues of 2-deoxy-D-glucose in solid state and solution>, Quality Control of 492-62-6, the main research area is deoxyglucose conformation electron density hydrogen bond supramol self assembly.
The structural studies on two bromo-substituted derivatives of 2-deoxy-D-glucose (2-DG), namely 2-deoxy-2-bromo-D-glucose (2-BG) and 2-deoxy-2-bromo-D-mannose (2-BM) are described. 2-DG itself is an inhibitor of hexokinase, the first enzyme in the glycolysis process, playing a vital role in both cancer cell metabolism and viral replication in host cells. Because of that, 2-DG derivatives are considered as potential anti-cancer and anti-viral drugs. An X-ray quantum crystallog. approach allowed us to obtain more accurate positions of hydrogen atoms by applying Hirshfeld atom refinement, providing a better description of hydrogen bonding even in the case of data from routine X-ray experiments Obtained structures showed that the introduction of bromine at the C2 position in the pyranose ring has a minor influence on its conformation but still, it has a noticeable effect on the crystal structure. Bromine imposes the formation of a layered supramol. landscape containing hydrogen bonds, which involves the bromine atom. Periodic DFT calculations of cohesive and interaction energies (at the B3LYP level of theory) have supported these findings and highlighted energetic changes upon bromine substitution. Based on mol. wavefunction from the refinement, we calculated the electrostatic potential, Laplacian, and ELI-D, and applied them to charge-d. studies, which confirmed the geometry of hydrogen bonding and involvement of the bromine atom with these intermol. interactions. NMR studies in the solution show that both compounds do not display significant differences in their anomeric equilibrium compared to 2-DG, and the pyranose ring puckering is similar in both aqueous and solid state.
RSC Advances published new progress about Bader electron density. 492-62-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H12O6, Quality Control of 492-62-6.
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts