Separating an Oxygen Atom in a Molecule



 Scientists have pulled an oxygen atom from a molecule and replaced it with a nitrogen atom. A group of chemists at the Korea Advanced Institute of Science and Technology have published in the journal Science. The team used photocatalysis to edit a furan in their lab.

In the same journal, Ellie Planchinski and Tehshik Yoon published a Perspective piece. These scientists were from the University of Wisconsin-Madison. Their research outlines the process and explains how it could be used to change how drugs are currently being made. Previous research has shown complex molecules are difficult to locate and apply. Chemists must create molecules from scratch when they want to change a small section, or part of a molecule, or even one atom for testing.

Both Plachinski and Yoon report that even small changes can have a serious impact. Changing a single atom in a heterocycle can have a big impact on the efficacy of a drug. Chemists are searching for more efficient ways to remove a single atom and replace it with another.

Scientists have a new technique they call pencil and eraser. Essentially, one atom is erased and another is penciled in.

In 1971, chemists Axel Couture and Alain Lablache-Combier wrote a related paper and the researchers in the study were inspired by it. They used ultraviolet light to convert a furan to a N-propylpyrrole as a way to increase yield. They used ultraviolet light to swap an oxygen atom in a furan with a nitrogen atom. 

This editing, the new team reports, is a challenge. This is due to issues with delocalization. Prior attempts have involved radiation or high temperatures. Neither approach is considered suitable for use.

In this new approach, scientists used light as a photocatalyst. The team used light to activate a furan ring. They found that this technique can be used as single electron oxidation on a furan. This oxidation results in radicalization.

This technique allows for a facile reaction. This is susceptible to the addition of amine. This leads to a transfer of protons between the product and the photocatalyst. The final results are a creation of a ring of aldehyde intermediate.


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