💥 Poison or medicine? The case of “mirror” molecules

2024-03-27 12:00:14

Enantiomers are two molecules of the same chemical composition, mirror images of each other, which do not overlap. Produced in equal quantities during the chemical reaction, they can exhibit opposite biological properties.

Isolating one of them then proves essential, but also very complex due to almost identical physical properties. Scientists propose a new strategy to simultaneously prepare and separate two enantiomers of the same molecule (A molecule is an electrically neutral chemical assembly of at least two atoms, which…).

A molecule is said to be chiral (from the Greek χείρ (kheír), the hand) when it can adopt two forms, called enantiomers, of the same chemical composition, images of each other in a mirror and not superimposable. Just like our two hands. Two enantiomers share the same physical properties except for the deviation of the light (Light is all electromagnetic waves visible to the eye…) polarized. On the other hand, in a biological environment, two enantiomers sometimes have different chemical properties: one enantiomer of a drug can have therapeutic properties while the other is toxic. Being able to have each of the enantiomers of a molecule is therefore crucial but also regulatory, particularly for clinical testing of new drugs.

During their synthesis, the two enantiomers are most of the time produced in equal quantity formant (In intonation, changes in fundamental frequency are perceived as variations in…) and mélange (A mixture is a combination of two or more solid, liquid or gaseous substances…) called “racemic”. It turns out to be very difficult to selectively synthesize only one of the two enantiomers. Several strategies were then developed to separate enantiomers from a racemic mixture.

For example, one of the two enantiomers can be selectively reacted using a chiral catalyst: this one is transformed while the other remains intact. The use of chiral membranes acting as filters to separate the two enantiomers is another way of research (Scientific research primarily refers to all actions undertaken with a view to…) also explored.

© Cyril Bressy & Damien Hérault

Scientists from the Marseille Institute of Molecular Sciences (CNRS/Aix-Marseille Université (A university is an establishment of higher education whose objective is…) / Centrale Méditerranée) propose an original strategy to simultaneously prepare and physically separate two enantiomers of a molecule from a racemic substrate.

This approach combines two chiral catalysts, images of each other in a mirror operating in parallel, and separation by a nonchiral membrane with selective permeability. Successfully tested on Jacobsen’s HKR model reaction which makes it possible to obtain chiral 1,2-diols* from racemic epoxides**, it could be extended to other reactions leading to key chiral building blocks in synthesis organic (Organic chemistry is a branch of chemistry concerning the description and study of a large…) or pharmaceutical. Results to be found in the Journal of the American Chemical Society.

Notes:
*A diol is an organic compound bearing two hydroxyl groups (-OH).
** Functional group where two carbon atoms are joined by a atom (An atom (from the Greek ατομος, atomos, “which one cannot…) d’oxygen (Oxygen is a chemical element from the chalcogen family,…).

Editor: CCdM

Reference:
Jingke Hou, Sabine Chevallier-Michaud, Marion Jean, Luc Favre, Damien Hérault & Cyril Bressy.
Physical Separation of Enantiomeric Products by Compartmentalized Parallel Kinetic Resolution
J. Am. Chem. Soc. 2023, 145, 27236-27241.

1711546674
#Poison #medicine #case #mirror #molecules