Development of chirality sensors beyond the current paradigm

Jan Labuta

Many pharmaceuticals are chiral compounds and when they are synthesized often both enantiomers are present. They need to be separated since they generally have different therapeutic effect. One enantiomer can have desirable therapeutic effect and the other can be even toxic (e.g. bupivacaine, thalidomide, etc.). The standard nuclear magnetic resonance (NMR) spectroscopy protocols of enantiomeric purity measurements are always based on formation of diastereomers (two mirror non-superimposable species). We have developed novel sensing method utilizing achiral porphyrin derivatives in which the diastereomers are not formed.^[1-4] The mechanism and potential applications will be discussed in this talk.

[1] J. Labuta, S. Ishihara, K. Ariga and J. P. Hill. Symmetry, 6, 345 (2014).

[2] J. Labuta, S. Ishihara, T. Šikorský, Z. Futera, A. Shundo, L. Hanyková, J. V. Burda, K. Ariga and J. P. Hill. Nat. Commun., 4, 2188 (2013).

[3] J. Labuta, S. Ishihara, A. Shundo, S. Arai, S. Takeoka, K. Ariga and J. P. Hill. Chem. Eur. J., 17, 3558 (2011).

[4] A. Shundo, J. Labuta, J. P. Hill, S. Ishihara and K. Ariga. J. Am. Chem. Soc., 131, 9494 (2009).