Novel bifunctional catalyst enables new applications
"Activation" of molecules by catalysts with two reactive sites
In a recent issue of the Journal of the American Chemical Society, the team led by Professors Johannes Teichert (Chair of Organic Chemistry) and Martin Breugst (Chair of Theoretical Organic Chemistry) from Chemnitz University of Technology presents their research findings on so-called "site-selective catalysis". "This type of selectivity can only be realized very rarely, as it represents a major challenge - namely the differentiation of different but very similar reactive sites within a molecule. This type of reaction is inspired by nature, as enzymes can often enable these site-selective reactions with high precision. However, it is very difficult to reproduce this with a man-made catalyst, as the accuracy of fit of the artificial compounds is often not high enough," explains Teichert.
Doubly reactive catalyst distinguishes between different amides
In the publication, the Chemnitz research team describes how a so-called "bifunctional catalyst" can be used to differentiate between structurally very closely related subunits of the molecules, namely two amides. Bifunctional means that two reactive subunits work hand in hand in the catalyst - one is responsible for recognizing the respective amide, while the other carries out the actual reaction, a so-called reduction, directly on the recognized amide. However, it is important to note that the two subunits are only effective if they are in close proximity to each other, i.e. if they are linked together in the same molecule.
The significance of the current work is underlined by the fact that no other catalyst or reagent has so far been able to distinguish between different amides. In this process, the researchers at Chemnitz University of Technology were able to identify several so-called "privileged amides", each of which is preferentially targeted by the catalyst - even if other amides are present in the same molecule. While these "privileged amides" are quickly converted by the catalyst, the "non-privileged amides" hardly react at all or only very slowly. This is the key finding that doctoral student Dimitrios-Ioannis Tzaras from the Organic Chemistry working group discovered during his research work.
Interplay between experiment and theory
In addition to the experiments, quantum mechanical calculations by Prof. Breugst's research group were also crucial for an initial fundamental understanding. "These calculations are an important piece of the puzzle when it comes to explaining the cause of the rare site selectivity, without which important findings would be missing here," says Breugst about the joint work.
Possible application in drug research or sustainable chemistry
Amides are important building blocks in both active ingredients and materials, which is why this work provides important insights for simpler production of complex biologically active molecules or, for example, for highly efficient plastic recycling with sustainable hydrogen. "We will continue to actively research in this direction in particular," says Teichert.
Note: This article has been translated using a computer system without human intervention. LUMITOS offers these automatic translations to present a wider range of current news. Since this article has been translated with automatic translation, it is possible that it contains errors in vocabulary, syntax or grammar. The original article in German can be found here.
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