Article
Chemistry, Multidisciplinary
Qianyue Hu, Qingming Li, Jie Tang, Jie Liu, Yi Fang, Chunyi Liu, Meihui Qi, Zhengping Chen
Summary: This study synthesized and evaluated a series of F-18-labeled deuterated N-fluoropropyl tropane derivatives as PET radioligands for DAT tracing. Among them, [F-18]4e, as a new probe with good DAT affinity, specificity, and metabolic stability, may provide reliable diagnosis, treatment, and prognostic detection of DAT-related neuropsychiatric diseases.
ARABIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Petri A. Turhanen
Summary: The chemical synthesis of the dideuterium-labelled ATP analogue ApppI(d2) is described, and its purification and characterization by various techniques are reported. The quantitative measurement of ApppI in biological samples is of great importance for the study of related diseases.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Xiaoli Yang, Haoxi Ben, Arthur J. Ragauskas
Summary: This review summarizes recent advances in the preparation methods of deuterium-labeled compounds, including conventional deuteration and hydrogen-deuterium exchange, with a focus on key features of hydrogen-deuterium exchange from the perspective of catalyst and chemical structure of the substrate, as well as the significance of stereospecific deuterium labeling in medicine.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Anna Pees, Maria J. W. D. Vosjan, Neil Vasdev, Albert D. Windhorst, Danielle J. Vugts
Summary: This article describes the first synthesis and application of fluorine-18 labelled Ruppert-Prakash reagent [F-18]Me3SiCF3, which was used to successfully prepare F-18-trifluoromethylated compounds by reacting with benzaldehydes, acetophenones and benzophenones.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Duanyang Kong, Maxime Munch, Qiqige Qiqige, Christopher J. C. Cooze, Benjamin H. Rotstein, Rylan J. Lundgren
Summary: Carbazole/cyanobenzene photocatalysts have been shown to promote direct isotopic carboxylate exchange of C(sp(3)) acids with labeled CO2, allowing for isotopic incorporation of substrates that are not compatible with traditional transition-metal-catalyzed degradation-reconstruction approaches or prone to thermally induced reversible decarboxylation at room temperature in short reaction times. The radiolabeling of drug molecules and precursors with [C-11]CO2 has been successfully demonstrated.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Soil Science
Charles R. Warren
Summary: The aim of this study was to develop D2O-labelling of intact polar lipids (D2O-intact lipid-SIP) as a culture- and gene-independent way of probing synthesis of membrane lipids by soil microbes. By coupling D2O labelling with liquid chromatography-mass spectrometry (LC-MS) quantification, and determining appropriate incubation durations, the researchers were able to quantify the 2H enrichment of a broad spectrum of lipids in soils incubated with 50 atom% D2O for 27 hours.
SOIL BIOLOGY & BIOCHEMISTRY
(2023)
Article
Chemistry, Organic
Alexey Dobrydnev, Andrii Tarasov, Maria Popova, Stefanie Fritsch, Heike Hausmann, Holger Zorn, Yulian M. Volovenko, Doris Rauhut, Rainer Jung
Summary: We present an economical and scalable synthesis method for TDN-D-3, a deuterium-labeled specimen used in stable isotope dilution assays. The synthesis involves four simple steps and can be completed in three part-time working days, resulting in TDN-D-3 with 25% overall yield and >99% purity. This method eliminates the need for additional purification procedures such as HPLC or column chromatography.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Medicinal
V. P. Shevchenko, I. Yu. Nagaev, A. V. Lopachev, N. F. Myasoedov
Summary: The efficiency of isotopic exchange using a homogeneous base (Et3N) and heterogeneous catalysts was compared. When using Et3N, the incorporation of deuterium into ouabain reached an average of about 3.26 atoms, but the yield was limited to 15-20%. The use of 5% Pd/BaSO4 catalyst was found to be the best for obtaining preparative amounts of labeled ouabain. The reaction carried out at 125oC for 30 min yielded a product with a 77% yield and an average content of 2.14 deuterium atoms per molecule. The use of heterogeneous catalysts simplified the purification process by reducing the number of by-products compared to Et3N.
PHARMACEUTICAL CHEMISTRY JOURNAL
(2023)
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
Andrii Malashchuk, Anton V. Chernykh, Alexey V. Dobrydnev, Oleksandr O. Grygorenko
Summary: A reliable methodology was developed for constructing the 6-fluoro-spiro[3.3]heptane scaffold, generating a library of functionalized building blocks with potential medicinal chemistry applications. The generated compounds demonstrate a high propensity to populate lead-like chemical space while retaining similar three-dimensionality features.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Zongqiang Song, Kai Zhu, Hongqiang Jiang, Hengfa Gong, Zenghui Ye, Fengzhi Zhang
Summary: A simple and novel method for the synthesis of 1,3-dioxepine-fused (tricyclic) bispyrazoles is described. The protocol involves O-alkylation and intramolecular oxidative biheteroaryl coupling under mild conditions. The synthesized compounds have potential applications in medicinal or material chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Pharmacology & Pharmacy
Yoshinari Sawama
Summary: Deuterium is a stable isotope of hydrogen and its labelled compounds have wide applications in various scientific fields. This paper summarizes the deuteration methods using organocatalysts and their applications. The obtained deuterated compounds can serve as important synthetic precursors for constructing deuterium-incorporated target functional materials.
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN
(2022)
Article
Chemistry, Multidisciplinary
Ester M. Di Tommaso, Per-Ola Norrby, Berit Olofsson
Summary: Vinylbenziodoxolones have been identified as efficient reagents for electrophilic vinylations under metal-free conditions. This paper presents the first mechanistic investigation of VBX vinylations, providing insights into the regio- and stereochemical outcome. The findings can be applied to predict the regioselectivity in vinylations of other nucleophile classes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jianbo Tang, Jian-Fei Bai, Jinfeng Zheng, Shuangshuang Li, Zhi-Jiang Jiang, Jia Chen, Kun Gao, Zhanghua Gao
Summary: A method for the deuteration of intra- and extra-cyclic methylene in cyclic ethers using D2O as a deuterium source has been developed, resulting in moderate yield and excellent deuterium incorporation. The transformation shows remarkable tolerance towards functional groups in a wide range of alkynols, and the key factor for achieving high deuterium incorporation is the hydrogen isotope exchange reaction of an unstable oxonium ion. This novel methodology provides an efficient and concise synthetic route to valuable deuterated cyclic ethers that are often challenging to prepare using other methods.
Article
Biotechnology & Applied Microbiology
Veronika Kselikova, Kamila Husarcikova, Peter Mojzes, Vilem Zachleder, Katerina Bisova
Summary: The autotrophic growth of two microalgae in medium containing high doses of deuterated water was investigated in this study. It was found that deuteration increased light sensitivity, resulting in decreased photosynthetic performance and growth. Impaired cell division led to cell enlargement and accumulation of highly deuterated compounds.
FRONTIERS IN BIOENGINEERING AND BIOTECHNOLOGY
(2022)