Study sheds light on the complex mechanisms that lead to biological homochirality



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## Study sheds light on the complex mechanisms that lead to biological homochirality

18/10/2022 |
SCP

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The research team of the Department of Inorganic and Organic Chemistry of the UJI has counted with the participation of Nobel Prize winner Jean-Marie Lehn.

Nature uses elegant ways to build complex architectures, such as macrocycles (molecules containing a ring of twelve or more atoms) or cages (three-dimensional molecular structures with cavities to house other molecules inside). Macrocycles or macrobicycles have been used for sophisticated applications since the birth of supramolecular chemistry, but the synthesis of pre-organised three-dimensional species has usually been a challenge.

On the other hand, nature employs a very large number of chiral molecules where atoms can organise themselves in space in two different ways — just as the fingers of the right hand and the left hand do — that appear identical, but are not superimposable. Surprisingly, the construction of many natural molecules such as proteins (from amino acids) or carbohydrates (from sugars) involves only one of these two arrangements (proteins are formed from S-type amino acids and not R-type amino acids), giving rise to the phenomenon known as *homochirality*. Understanding how this biological homochirality has come about is an essential topic in the natural sciences.

The Sustainable and Supramolecular Chemistry research team of the Department of Inorganic and Organic Chemistry formed by Eduardo García-Verdugo, Belén Altava, Santiago V. Luis and Ferran Esteve, together with Nobel Laureate Jean-Marie Lehn, has succeeded in describing the dynamic covalent self-assembly — assisted by water — of novel doubly chiral pseudopeptidic macrobicyclic double-chiral molecular cages, with a very efficient self-selection of homochirality. This work has been published in the July issue of the journal *Chem*.

Although there are some already described examples of homochiral self-selection, the design proposed by this team can shed light on the complex mechanisms that lead to it by revealing that water encapsulation is essential for it, thus showing a non-biological example of the role of water in the formation of sophisticated molecules that mimic biological behaviours. Indeed, the encapsulation of discrete water molecules appears to be the main driving force behind this error-checking process, acting as a positive template to stabilise three-dimensional homochiral cavities and facilitate their formation.

These results highlight the role of the aqueous medium in the efficiency and selectivity of formation, as well as in determining the structural characteristics of the complex three-dimensional architectures adopted by the biomolecules. The structure of these molecular cages and the process of their formation have been analysed in depth by means of X-ray diffraction studies and H-NMR spectroscopy.

The study was dedicated to the 80th birthday of Professor Alain Krief. It has been financially supported by the European Research Council, the Advanced Institute of the University of Strasbourg (USIAS), the Research Promotion Plan of the Universitat Jaume I of Castelló and the State Research Agency of the Ministry of Science and Innovation with FEDER funds.

**Interview with Professor Lehn**

On the occasion of his participation in the jury of the Jaume I Awards of the Generalitat Valenciana, Professor Jean-Marie Lehn visited the public university of Castelló at the invitation of the Department of Inorganic and Organic Chemistry, with whose research staff he has a working relationship. The Nobel Laureate in Chemistry had a relaxed chat with Eduardo García-Verdugo, head of the Sustainable and Supramolecular Chemistry Group, and Ferran Esteve, who had carried out a research stay during his doctoral studies with Professor Lehn at the Supramolecular Chemistry Laboratory of the Institute of Supramolecular Sciences and Engineering of the University of Strasbourg.

**Article**

“Doubly chiral pseudopeptidic macrobicyclic molecular cages: water-assisted dynamic covalent self-assembly and chiral self-sorting”, Ferran Esteve, Belén Altava, Eduardo García-Verdugo, Santiago V. Luis and Jean-Marie Lehn. Revista *Chem*. Volume 8, issue 7, 14 July 2022, pages 2023-2042.

<https://www.sciencedirect.com/science/article/abs/pii/S2451929422002029>

**Image** (from left to right): Eduardo García-Verdugo, Jean-Marie Lehn, Ferran Esteve and Santiago V. Luis.

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