Chiral Technologies, a wholly owned subsidiary of Daicel Corporation, is the global leader in enantioselective chromatography, serves pharmaceutical and other life science industries and offers the largest portfolio of chiral stationary phases (CSPs) and analytical and preparative chiral columns for the separation of racemic mixtures into single enantiomers. In addition, the company also supplies bulk chiral stationary phases and operates an outsourcing center for separation of chiral intermediates and APIs in pre-clinical and clinical evaluations.
Chiral Technologies serves the North and Latin American markets through Chiral Technologies Inc. (West Chester, Pa.), the European market through Chiral Technologies Europe SAS (Illkirch, France), and the Asian market through Daicel Chiral Technologies India and Daicel Chiral Technologies China, all wholly owned subsidiaries of Daicel Corporation.
Chirality in chemistry was first identified by the French physicist Biot in the early 1800s and in 1848, Louis Pasteur reported the first chiral separation of racemic sodium ammonium tartrate to obtain enantiomers of the racemic molecule. Van’t Hoff, the Dutch physical chemist, was the first to propose that the molecular basis of chirality was an asymmetric carbon center.
Enantiomers are mirror images of one another that are non-superimposable. Enantiomers, or optical isomers, rotate plane polarized light in different directions, whereas racemic mixtures are optically inactive.
Due to disastrous side-effects of some racemic drugs (most notably thalidomide) the FDA issued guidelines for development of new racemic drugs, requiring companies to evaluate and report pharmacology and toxicity profiles of a racemate and its enantiomers prior to beginning clinical trials. Clearly, the availability of appropriate analytical methods for determining/monitoring enantiomeric composition is critical to ascertain toxicity and biological activity of pure enantiomers or their mixtures.
In recent years, the use of chiral chromatography has become well accepted as an effective, rapid and direct method to obtain pure enantiomers. Chiral stationary phases (CSPs) must contain chiral selectors that provide enantiorecognition for chiral molecules. To be effective, a CSP must have different affinity for each of the two enantiomers in a racemic mixture.
There are a number of CSPs that are commercially available, but the most popular and effective are based on polysaccharides such as amylose and cellulose. These types of CSPs have been proven to be the most general and easy to use options for chiral chromatography.
Polysaccharide-derived chiral selectors were invented by Professor Yoshio Okamoto of Nagoya University in Japan, while he was conducting research in the field of synthetic optically active polymers. Daicel Corporation commercialized Professor Okamoto’s inventions, which are the foundation of the highly successful and widely used Daicel chiral stationary phases (CSPs) – Chiral Technologies’ core technology.
Our chiral chromatography products range from analytical columns, to preparative columns, to bulk CSP for commercial-scale separations, with particle sizes of the CSPs varying depending on the application.
HPLC separations are carried out globally using a range of equipment depending on the scale of the separation desired. Chiral Technologies performs enantiomer resolution of chiral compounds, starting from a few milligrams to multi-kilograms in quantities. HPLC separations can be carried out under cGMP if required.
Chiral Technologies operates state-of-the-art HPLC equipment to maximize the sample throughput and to ensure that projects are completed on time. Solvents are recovered and recycled during any one project, reducing the overall solvent use to minimize the environmental impact and to lower the costs of the separation.
With the introduction of small diameter particles (< 2 µm), HPLC instruments needed to be improved to provide the potential benefits offered by these columns. A number of Ultra-High Performance Liquid Chromatography (UHPLC) systems are now available from HPLC manufacturers. UHPLC systems utilize high-pressure pumps and low extra-column dispersion by minimizing volumes of connecting tubing, detection flow cells and employing high-speed data acquisition units.
UHPLC is the generic industry term, however UPLC (Ultra Performance Liquid Chromatography) is a trademarked name, commonly used when referring to this subject. Both are the same technique and both are a specialized subset of HPLC.
The introduction of the sub-2 µm immobilized chiral columns by Daicel Corporation will allow an increase in resolution and speed for UHPLC chiral chromatography.
SFC has become a popular technique for preparative chromatography. Chiral Technologies has been at the forefront of the technology establishing separation services in 1997. Chiral Technologies has also developed semi-preparative chiral columns specifically designed for SFC applications.
SFC has two main advantages for a number of preparative separations. One is speed: a higher production rate can be obtained since the mobile phase viscosity is very low and fast, efficient separations can be achieved. The other advantage is the small volume of organic solvent used: between 10% and 20% of that needed for a HPLC separation. This not only decreases the total solvent consumption used for the separation, but also makes it easier and faster to recover the products from the small modifier volumes remaining after condensation from the CO2.
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