Chiral Resolution

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Chiral Resolution

Chiral resolution, as an important tool in the production of optically active drugs, is a process for the separation of racemic compounds into their enantiomers in the aspect of stereochemistry. Particularly when the methods of stereospecific synthesis designed for one of the enantiomers, at present, lead generally to enhanced enantioselectivity, not only the development of analytical methods for the chiral separation to control optical purity of a large number of pharmaceuticals/therapeutics, administered today, but also the development of methods for quantitative large-scale separation from their racemic or enantiomeric mixture are required and are the challenges for chemists and open wider perspectives for such developments.

Chiral Resolution Figure 1. Methods to obtain enantiomerically pure compounds by means of chiral resolution

Below is a list of our chiral resolution method (include but not limited to the following):

Chiral resolution by crystallization

The separation of racemates into pure enantiomers through crystallization is an important industrial process. Racemic compounds are known to crystallize as mixtures of enantiopure crystals, so-called conglomerates. If the racemate is a true racemic mixture, then it cannot be separated by preferential crystallization, but can be resolved using the diastereomer crystallization.

Lipase-catalyzed kinetic resolution of racemates is considered to be one of the most fascinating topics in asymmetric catalysis. Most lipases accept a broad range of non-natural substrates and are thus very versatile for applications in organic synthesis. In many cases, they exhibit well to excellent stereoselectivity. Lipases have been widely used in three main types of reactions yielding enantiomerically pure compounds. These are kinetic resolutions of racemic carboxylic acids or alcohols, enantioselective group differentiations of meso dicarboxylic acids or meso diols and enantiotopic group differentiation of prochiral dicarboxylic acid and diol derivatives.

The third method used in the resolution of racemates is the kinetic resolution. The success of this method is dependent on the fact that the two enantiomers react at different rates with a chiral entity. The chiral entity should be present in catalytic amounts; it may be a biocatalyst (enzyme or a microorganism) or a chemocatalyst (chiral acid or base or even a chiral metal complex). Kinetic resolution of racemic compounds is by far the most common transformation catalyzed by lipases, in which, the enzyme discriminate between the two enantiomers of racemic mixture, so that one enantiomer is readily transferred to the product faster than the other.

BOC Sciences has accumulated abundant experience in chiral resolution, and we can provide comprehensive and professional service for your requirements. Our featured chiral resolution services include resolution by crystallization, resolution by Lipase-mediated in organic solvents and so on. There are a large number of instruments and enormous seasoned experts in our company. BOC Sciences’s mission is to using professional technologies and knowledge for the benefit of customer.

Reference

  1. Ghanem, A., & Aboul-Enein, H. Y. (2004). Lipase-mediated chiral resolution of racemates in organic solvents. Tetrahedron: Asymmetry15(21), 3331-3351.
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