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Related Concept Videos

Racemic Mixtures and the Resolution of Enantiomers02:30

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A racemic mixture, or racemate, is an equimolar mixture of enantiomers of a molecule that can be separated using their unique interaction with chiral molecules or media. Racemic mixtures are denoted by the (±)- prefix. This ‘optical rotation descriptor’ applies to the whole solution of a racemic mixture rather than a specific stereoisomer. Enantiomers typically have the same physical and chemical properties. Hence, they are not easily separable. However, enantiomers can exhibit...
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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
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Deuterium-Enabled Chiral Switching (DECS) Yields Chirally Pure Drugs from Chemically Interconverting Racemates.

Sheila DeWitt1, Anthony W Czarnik1, Vincent Jacques1

  • 1DeuteRx, LLC, 300 Brickstone Square, Suite 201, Andover Massachusetts 01810, United States.

ACS Medicinal Chemistry Letters
|October 16, 2020
PubMed
Summary
This summary is machine-generated.

Chiral switching stabilizes unstable drugs by replacing hydrogen with deuterium, enabling enantiomer separation. This deuterium-enabled chiral switching (DECS) improves drug efficacy and reduces toxicity for unstable racemates.

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Pharmacology

Background:

  • Chiral switching, separating enantiomers from racemates, can enhance drug efficacy and reduce toxicity.
  • This strategy is limited for chiral compounds with hydrogen-containing chiral centers prone to stereoisomerization.

Purpose of the Study:

  • To introduce deuterium-enabled chiral switching (DECS) as a method to stabilize chemically unstable racemic drugs.
  • To demonstrate DECS utility by isolating stable enantiomers of thalidomide and thiazolidinedione (TZD) analogs.

Main Methods:

  • Deuterium incorporation to stabilize chiral centers in racemic mixtures.
  • Isolation and characterization of stable preferred enantiomers.

Main Results:

  • Successful stabilization of chiral centers through deuterium incorporation.
  • Isolation and characterization of stable enantiomers of thalidomide and TZD analogs were achieved.

Conclusions:

  • Deuterium-enabled chiral switching (DECS) offers a viable strategy for improving unstable racemic drugs.
  • DECS facilitates chiral switching for compounds previously unsuitable due to stereoisomerization instability.