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Concept
Synthèse asymétrique
Résumé
Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts."
Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer. Enantiomers are stereoisomers that have opposite configurations at every chiral center. Diastereomers are stereoisomers that differ at one or more chiral centers.
Enantioselective synthesis is a key process in modern chemistry and is particularly important in the field of pharmaceuticals, as the different enantiomers or diastereomers of a molecule often have different biological activity.
Many of the building blocks of biological systems such as sugars and amino acids are produced exclusively as one enantiomer. As a result, living systems possess a high degree of chemical chirality and will often react differently with the various enantiomers of a given compound. Examples of this selectivity include:
Flavour: the artificial sweetener aspartame has two enantiomers. L-aspartame tastes sweet whereas D-aspartame is tasteless.
Odor: R-(–)-carvone smells like spearmint whereas S-(+)-carvone smells like caraway.
Drug effectiveness: the antidepressant drug Citalopram is sold as a racemic mixture. However, studies have shown that only the (S)-(+) enantiomer is responsible for the drug's beneficial effects.
Drug safety: D‐penicillamine is used in chelation therapy and for the treatment of rheumatoid arthritis whereas L‐penicillamine is toxic as it inhibits the action of pyridoxine, an essential B vitamin.
As such enantioselective synthesis is of great importance but it can also be difficult to achieve. Enantiomers possess identical enthalpies and entropies and hence should be produced in equal amounts by an undirected process – leading to a racemic mixture.
Source officielle
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