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Related Concept Videos

Racemic Mixtures and the Resolution of Enantiomers02:30

Racemic Mixtures and the Resolution of Enantiomers

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 different...
Phase I Reactions: Reductive Reactions01:27

Phase I Reactions: Reductive Reactions

Phase I biotransformation reductive reactions are chemical processes that modify drugs by introducing or revealing polar functional groups via reduction. Enzymes called reductases catalyze these reactions, playing a pivotal role in drug metabolism by transforming lipophilic drugs into more polar, water-soluble metabolites for easy excretion. An essential type of reductive reaction is the carbonyl group reduction, where aldehydes and ketones are reduced to alcohols. An example is the...
Oxymercuration-Reduction of Alkenes02:36

Oxymercuration-Reduction of Alkenes

Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
Radical Formation: Elimination00:51

Radical Formation: Elimination

Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect to...
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives01:35

Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.

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Updated: Jun 17, 2026

Quantitative Proteomics Using Reductive Dimethylation for Stable Isotope Labeling
11:53

Quantitative Proteomics Using Reductive Dimethylation for Stable Isotope Labeling

Published on: July 1, 2014

Deracemisation methods.

Nicholas J Turner1

  • 1School of Chemistry, University of Manchester, Manchester Interdisciplinary Biocentre, 131 Princess Street, Manchester M1 7DN, UK. nicholas.turner@manchester.ac.uk

Current Opinion in Chemical Biology
|January 2, 2010
PubMed
Summary
This summary is machine-generated.

New methods for dynamic kinetic resolution (DKR) and deracemisation of chiral compounds are advancing. Enzymes combined with metal catalysts, particularly ruthenium, show improved efficiency for alcohols and amines.

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Area of Science:

  • Organic Chemistry
  • Biocatalysis
  • Asymmetric Synthesis

Background:

  • Chiral compounds are crucial in pharmaceuticals and fine chemicals.
  • Developing efficient methods for enantioselective synthesis remains a key challenge.
  • Dynamic kinetic resolution (DKR) and deracemisation offer powerful strategies for obtaining enantiopure compounds.

Purpose of the Study:

  • To review recent advancements in DKR and deracemisation techniques.
  • To highlight the role of enzymes and metal catalysts in these processes.
  • To discuss the application of these methods to alcohols, amines, and amino acids.

Main Methods:

  • Utilisation of enantioselective enzymes (lipases, proteases, ketoreductases, transaminases).
  • Integration of metal racemisation catalysts, with a focus on ruthenium complexes.
  • Development of stereocomplementary enzyme systems for deracemisation.

Main Results:

  • Improved DKR processes combining enzymes and metal catalysts.
  • Ruthenium catalysts demonstrate enhanced activity for amine racemisation.
  • Successful deracemisation of alcohols using stereocomplementary ketoreductases.
  • Application of transaminases for the deracemisation of racemic amines.

Conclusions:

  • Significant progress has been made in DKR and deracemisation methodologies.
  • The combination of biocatalysis and chemocatalysis is a fruitful approach.
  • These advancements provide more efficient routes to enantiopure alcohols and amines.