Deuteration of Alkenes Based on DCL™
Background & Overview
Deuterium-labeled compounds are valuable probes in many studies, including reaction mechanisms, kinetics, and structural elucidation of biological macromolecules. Selective deuteration has also been identified as one of the most promising tools in drug design to improve their pharmacokinetic and pharmacodynamic properties. In order to improve the shortcomings of the common deuterium technology on the market, such as high cost, harsh reaction conditions, functional group intolerance, weak regioselectivity, etc., we have developed a proprietary DCL™ technology platform. Our platform enables the specific deuteration of alkenes through a selective H/D exchange process using inexpensive deuterium oxide as an isotope source.
Application of Deuterated Alkenes
The deuteration of alkenes has high application value. Taking deuterated ethylene (C2H4) as an example, as a special isotope gas with special functions, deuterated ethylene can be used as an intermediate of laser target materials, and is widely used in pharmaceutical synthesis, special engineering plastics and construction of important engineering projects. Its large-scale industrial production has very broad market prospects and extremely important social benefits.
Additionally, recent studies have shown that the lipid peroxidation process (LPO) of polyunsaturated fatty acids (PUFAs) leads to lipid membrane damage and protein/DNA damage, while site selectivity at their bisallyl sites Isotopic fortification has been identified as a unique approach to preventing oxidative damage to these molecules, which have been implicated in neuronal and retinal disease, atherosclerosis and aging. At the same time, the importance of deuterated alkenes also shows that the development of deuterated technology is invaluable for the further exploration and clinical application of these biologically important molecules.
Fig.1 Site-Specific Deuteration of Polyunsaturated Alkenes.[2]
Existing Strategy for the Synthesis of Deuterated Alkenes
Chemical synthesis and H/D exchange reactions are the two most common methods for introducing deuterium atoms. Chemical syntheses can utilize well-known reaction conditions for hydrogen-containing reagents; however, this approach suffers from numerous synthetic steps and low yields in most cases. H/D exchange is the process of exchanging active hydrogen in compounds with active deuterium in deuterated molecules under the catalysis of transition metals to induce C-H activation. At present, the synthesis of deuterated alkenes is mainly achieved by hemi-deuterated alkynes and transition metal-catalyzed H/D exchange reactions of alkenes.
Fig.2 Synthesis of Deuterated (E)-Alkene through Xanthate-Mediated Hydrogen–Deuterium Exchange Reactions.[3]
DCL™ in Deuteration of Alkenes
Unlike previous deuterated reactions, our DCL™ technology is based on a new multifunctional catalytic system that accomplishes the H/D exchange of olefins while providing excellent control over isomerization as it occurs. In addition to olefins, polyolefins, our technology also has potential applications in the deuteration of alkynes, polyenes and halides.
References
- Erdogan G, Grotjahn D B. Mild and selective deuteration and isomerization of alkenes by a bifunctional catalyst and deuterium oxide. Journal of the American Chemical Society. 2009, 131(30): 10354-10355.
- Smarun A V, et al. Site-specific deuteration of polyunsaturated alkenes. The Journal of Organic Chemistry. 2017, 82(24): 13115-13120.
- Li J, et al. Synthesis of Deuterated (E)-Alkene through Xanthate-Mediated Hydrogen–Deuterium Exchange Reactions. Organic Letters. 2021, 23(19): 7412-7417.
Customer Intellectual Property Protection
BOC Sciences has always regarded intellectual property as the most valuable asset of the company and its customers. We have signed non-disclosure agreements with customers and employees before the project starts, and provide synthetic route design and synthesis services in strict accordance with the terms of the non-disclosure agreement, striving to provide customers with target compounds in the shortest time possible.
