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A Light Approach to Installing Heavy Hydrogens

Friday, November 10, 2017   (0 Comments)
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Photoredox catalysis shines in a reaction that swaps out hydrogen for deuterium or tritium

To follow the fate of a drug or a drug metabolite as it wends its way through the body, scientists will often label the compound by switching out a hydrogen atom for one of its heavier isotopes—deuterium or tritium. This molecular switcheroo sounds simple, but it can actually be a lot of work, requiring chemists to resynthesize a molecule so it has an atom, usually a halogen, or unsaturated bond where the heavy hydrogen can be swapped in or added. The process can take months.

Chemists at Princeton University and Merck & Co. have now come up with a way to switch hydrogen out for deuterium or tritium in a matter of moments. The reaction uses photoredox-mediated hydrogen-atom transfer to replace the hydrogens at C–H bonds adjacent to amines with deuterium or tritium from D2O or T2O (Science 2017, DOI: 10.1126/science.aap9674).
Amines are common motifs in biologically active molecules, and the chemists, led by Princeton’s David W. C. MacMillan, show the reaction works on myriad drug molecules (examples shown). For the tritiation reactions, the chemists also figured out how to make T2O, which isn’t commercially available, during the reaction using T2 gas and platinum oxide.

The new labeling methodology could “open the door to earlier and expanded use of isotopic labeling in drug discovery, significantly enhancing our ability to study drug candidates on a deeper level and across a range of applications,” says Jennifer Lafontaine, senior director of synthesis and analytical chemistry in Pfizer’s oncology medicinal chemistry group.


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