Chiral applications databases

Figure 10-5. The 2005 version of the ChirBase LC chiral applications database contains over 100,000 entries.

Application databases have been particularly popular in the world of chiral method development (Figure 10-5). While it has been observed that small changes in compounds can result in loss of effectiveness (separation selectivity) for a given method, the results of searches can be used to create targeted method screens that can reduce the time and expense of development [36]. 

Chiral selectors are routinely used in industry for a wide variety of applications and there have been many reports published describing their use in CE for the enantiomeric separations of pharmaceutical compounds. A quick search of scientific databases will yield a far greater number of publications dealing with chiral CE than is possible to cover in this chapter however. Table 4.2 contains a selection of such applications and details of carrier electrolytes used. Readers are referred to review papers [16,63,64,116,107,141-144], which comprehensively cover recent chiral applications of CE and provide more detailed theory about chiral separations and detection methods. 

It would require a Herculean effort to prepare a complete discussion and review of every report related to the synthesis, reaction, or application of an oxazole while tabulating every oxazole, oxazolone, oxazoline, and chiral bis(oxazoline) prepared and evaluated during the period of 1983-2001. Such an undertaking is beyond the scope of this review. Furthermore, the ease with which electronic databases, including the patent literature, can be searched, the data retrieved, and the information tabulated would render such a project somewhat redundant. 

Figure 2.150. Ligprep is used for the rapid conversion of 2D structure files into accurate 3D models suitable for use in database screens and other applications. At the user s discretion Ligprep can generate multiple protonation states, enumerate chiralities, and generate tautomeric forms of the ligand...

The main applications of enantiomeric separation by GC concern precise determination of enantiomeric composition of chiral research chemicals, drugs, intermediates, metabolites, pesticides, flavors and fragrances, etc. CHIRBASE, a database of chiral compounds, provides comprehensive structural, experimental, and bibliographic information on successful and unsuccessful chiral separations, and rule sets for each CSP and information about the processes of chiral separations. According to CHIRBASE, an appropriate CSP is available for almost every racemic mixture of compounds ranging form apolar to polar. Some 22,000 separations of enantiomers, involving 5,500 basic chiral compounds and documented in 2,200 publications, have been achieved by GC. This method is particularly suitable for volatile compounds such as inhalation anesthetic agents, e.g., enflurane, isoflurane, desflurane, and racemic a-ionone. 

Roussel C, Pierrot-Sanders J, Heitmann I, Piras P. CHIRBASE database current stams and derived research applications using molecular similarity, decision tree and 3D enantiophore search. In Subramanian G, editor. Chiral Separation Techniques. A practical Approach. 2nd edition. Weinheim Wiley-VCH 2001. p 95-125. 

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