Article
Chemistry, Medicinal
Klaus Gjervig Jensen, Claus Tornby Christoffersen, Mette Graulund Hvenegaard, Michael Didriksen, Morten Jorgensen
Summary: This study investigates the N-demethylation of Zicronapine and its deuterated analogs in a human in vitro metabolism system. The deuteration of the benzene ring was found to significantly reduce the rate of N-demethylation, while deuteration of the N-methyl group further decreased the reaction rate. This unprecedented 'distal kinetic isotope effect' observed in human liver microsomes and CYP450 liver enzymes should be given attention.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Biochemistry & Molecular Biology
Zhichao Ma, Lintao Zhang, Zhiyuan Cui, Xin Ai
Summary: This work investigates the influence of deuteration on the photophysical property and stability of luminescent radicals for the first time. Four deuterated radicals based on biphenylmethyl, triphenylmethyl, and deuterated carbazole were synthesized and characterized. The deuterated radicals exhibited excellent redox stability, as well as improved thermal and photostability. The appropriate deuteration can effectively suppress the non-radiative process, resulting in an increase in photoluminescence quantum efficiency (PLQE).
Article
Chemistry, Multidisciplinary
Andreu Tortajada, Eva Hevia
Summary: In this study, the combination of a simple sodium amide and a tridentate Lewis donor was shown to catalytically promote hydrogen isotope exchange of nonactivated arenes under mild reaction conditions. The ability to partially metalate C6D6 and generate specific intermediates was demonstrated as the key to catalytic deuteration.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Fei-Fei Sheng, Jian-Guo Gu, Kai-Hui Liu, Hong-Hai Zhang
Summary: This study presents a highly efficient and easily manipulated palladium-catalyzed H/D exchange protocol for the synthesis of beta-deuterated N-protected amino amides, which can be converted to beta-deuterated amino acids by removing protecting groups. The use of pivalic acid as an additive also promoted the successful deuterium labeling of phenylalanine derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jian-Guo Gu, Cai-Xia Wang, Guang-Qi Hu, Kang Shen, Hong-Hai Zhang
Summary: This study reveals the K2CO3/18-crown-6-catalyzed H/D exchange of heretoarenes in high atom % deuterium incorporation. The use of a weak base as a catalyst demonstrates excellent site selectivity and broad functional group tolerance. Control experiments confirm the essential role of removable bromide directing group in enhancing adjacent C-H bond reactivity, and bromide conversion to other functional groups is performed to construct useful deuterated compounds.
Article
Energy & Fuels
Ameen A. Al-Muntaser, Mikhail A. Varfolomeev, Muneer A. Suwaid, Dmitriy A. Feoktistov, Chengdong Yuan, Alexander E. Klimovitskii, Bulat I. Gareev, Richard Djimasbe, Danis K. Nurgaliev, Sergey I. Kudryashov, Ekaterina V. Egorova, Artem V. Fomkin, Oleg V. Petrashov, Igor S. Afanasiev, Gennady D. Fedorchenko
Summary: The study investigates the role of water in catalytic and non-catalytic aquathermolysis using isotope tracing techniques. The results demonstrate the chemical role of water as a green hydrogen donor solvent, and show that introducing a catalyst can significantly improve the upgrading performance. The findings not only enhance the theoretical understanding in this field, but also support the use of catalysts in aquathermolysis for enhanced in-situ heavy oil upgrading.
Article
Food Science & Technology
Ryan M. Parente, Paul M. Tarantino, Bradford C. Sippy, George A. Burdock
Summary: Deuteration as a means of altering caffeine's effects and duration of activity is unexplored. d9-Caffeine, a deuterated isotopologue of caffeine, may offer an alternative with less frequent consumption, lower doses, and reduced exposure to caffeine metabolites. Characterization of d9-caffeine's genotoxic potential and pharmacokinetic behavior is critical in understanding its differences from caffeine.
FOOD AND CHEMICAL TOXICOLOGY
(2022)
Article
Chemistry, Organic
Binlin Zhao, Qiuzhu Wang, Tianxiang Zhu, Bin Feng, Mengtao Ma
Summary: In this study, a palladium-catalyzed method was developed to synthesize structurally diverse C-1 deuterated aldehydes from readily available arenes, achieving deuterium incorporation with high selectivity (96%-99%). The cost-effective DCOONa was used as a convenient deuterium source under palladium-catalytic redox neutral conditions. This catalytic approach enables direct late-stage C-H functionalization of bioactive molecules and natural product derivatives assisted by C(sp(2))-H thianthrenation, and can also be applied to prepare deuterated drugs and analogues with high levels of deuterium incorporation.
Article
Chemistry, Organic
Guang-Qi Hu, Jing-Wen Bai, En-Ci Li, Kai-Hui Liu, Fei-Fei Sheng, Hong-Hai Zhang
Summary: A new method for deuterating (hetero)aryl bromides using Ag2CO3 as catalyst and D2O as deuterium source is disclosed in this study, which is highly efficient and easy to manipulate. In comparison to traditional multistep syntheses, this method allows for one-step deuterium labeling of various bioactive druglike molecules and key intermediates of functional materials. Additionally, this method demonstrates unique site-selectivity in comparison to existing transition-metal-catalyzed processes, leading to multideuterated (hetero)aryl bromides in one step.
Article
Chemistry, Analytical
Saba Aslani, Daniel W. Armstrong
Summary: Deuterium substitution in drug molecules has various benefits, such as improving pharmacokinetic properties and reducing toxicity and epimerization. The position of deuterium substitution also affects the properties of drug molecules. Therefore, studying low molecular weight deuterated isotopologues, which are the building blocks of larger deuterated molecules, is important. The retention of 23 deuterated isotopologues on different gas chromatography stationary phases was evaluated, and it was found that the polarity of the stationary phase affects the chromatographic isotope effects.
Review
Chemistry, Multidisciplinary
Gaurav Prakash, Nilanjan Paul, Gwyndaf A. Oliver, Daniel B. Werz, Debabrata Maiti
Summary: C-H deuteration is an important method for site-selectively deuterating organic frameworks, and its significance in pharmaceutical chemistry has been recognized. Deuterium labelled compounds have gained attention due to their pharmacological importance, and hydrogen isotope exchange (HIE) is the most common and efficient method for site-selective deuteration.
CHEMICAL SOCIETY REVIEWS
(2022)
Review
Chemistry, Multidisciplinary
Marco Lepron, Marion Daniel-Bertrand, Gabriel Mencia, Bruno Chaudret, Sophie Feuillastre, Gregory Pieters
Summary: Hydrogen isotope exchange (HIE) reactions have shown significant progress in recent years, playing a crucial role in the synthesis of tritium and deuterium-labeled compounds, as well as in improving the ADME properties of bioactive molecules. Nanocatalysis has been demonstrated as an effective tool for regio- and chemoselective labeling of complex molecules, bridging the gap between homogeneous and heterogeneous catalysis.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Review
Materials Science, Paper & Wood
Yan Song, Xianzhi Meng, Wei Jiang, Barbara R. Evans, Haoxi Ben, Yuanming Zhang, Yunqiao Pu, Sai Venkatesh Pingali, Brian H. Davison, Sai Zhang, Guangting Han, Arthur J. Ragauskas
Summary: Deuterated cellulose has significant applications in neutron scattering studies, providing insights into the structure and interactions of cellulose in plant cell walls.
Article
Chemistry, Multidisciplinary
Tao He, Hendrik F. T. Klare, Martin Oestreich
Summary: Superelectrophilic silylium/arenium ions are effective in exhaustivedeuteration of electron-deficient aryl halides. Using inexpensive C6D6as the deuterium source, excellent degrees of deuteriumincorporation were achieved under ambient conditions. This method allows the preparation of expensive or noncommercially available NMR solvents.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Biochemistry & Molecular Biology
Robin A. de Graaf, Monique A. Thomas, Kevin L. Behar, Henk M. De Feyter
Summary: Deuterium metabolic imaging (DMI) is a novel 3D magnetic resonance method for mapping metabolism of deuterated substrates in vivo. The study found that metabolic rates are only slightly affected by deuterium kinetic isotope effects, indicating potential for further development of quantitative DMI studies to generate metabolic flux maps in vivo.
ACS CHEMICAL NEUROSCIENCE
(2021)