Deuteration of Indole Compounds Based on DCL™
Background & Overview
The versatility of deuterium-labeled compounds has driven advances in strategies to efficiently obtain them. Indole is arguably the most ubiquitous heterocyclic compound in nature and is essential to our lives. They are rich in nucleic acids, vitamins, antibiotics, hormones, alkaloids, and pigments. Indole derivatives are widely used in the production of numerous industrial products, from pharmaceuticals and pesticides to herbicides. Because of the great potential of deuterium-labeled indoles, researchers were drawn to study new ways to incorporate deuterium into indoles.
BOC Sciences' DCL™ platform enables efficient, direct, and controllable indole deuteration strategies using more cost-effective catalysts and deuterium sources. Our practical and simple protocols can be implemented not only by organic chemists but also by researchers in other fields.
DCL™ in Deuteration of Indole Compounds
Our deuterated platform is designed to achieve regioselective binding of deuterium atoms to various sites in indole with high overall efficiency. In our hydrogen-deuterium exchange system, D2O is used instead of expensive D2 or CD3OD as the deuterated agent. In addition to mono- and di-deuteration of indole, tri-deuteration products can also be obtained with high efficiency. A good deuteration rate is maintained even after the dissociation of the directing group (DG).
Fig.1 Synthesis of Polydeuterated IAA and IBA in an Economical Way.[1]
We achieved optimization studies for deuteration by testing various reaction parameters, including catalyst, solvent, temperature, and time. Specifically, it includes the use of composite catalysts, prolonging the reaction time, and adjusting the reaction temperature.
Our Abilities
Optimizing the setup of the reaction conditions not only greatly improves the deuteration efficiency, but also helps to enrich the substrate range in our hydrogen-deuterium exchange reactions. Our extensive deuteration capabilities include, but are not limited to: indole acetic acid (IAA), indole butyric acid (IBA), L-tryptophan, N, O-dimethyl-IBA, indomethacin, yohimbine hydrochloride, carbazole, 7-ethylindole, 5-methylindole, 4-methylindole, 2-methylindole, 1-ethylindole, harmine hydrochloride and 3-(5-chloroindol-3-yl)-propionic acid methyl ester, etc.
In particular, our reaction system is highly suitable for the preparation of deuterated melatonin, a widely used treatment for insomnia, with high deuterium labeling rate and good separation yield.
Fig. 2 Deuterium Labeling of Melatonin.[2]
The efficient regioselective indole deuteration method possessed by BOC Sciences will open a new avenue for the synthesis of novel deuterated compounds, and we will continue to develop more promising and valuable organic compounds.
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.
References
- Yamada T, et al. Deuteration of Indole Compounds: Synthesis of Deuterated Auxins, Indole-3-acetic Acid-d5 and Indole-3-butyric Acid-d5. ACS omega. 2021, 6(30): 19956-19963.
- Zhang J, et al. Versatile regioselective deuteration of indoles via transition-metal-catalyzed H/D exchange. ACS Catalysis. 2020, 10(14): 7486-7494.
