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A dynamic combinatorial library composed of racemic hydrazone-based dipeptides becomes deracemized on binding to the chiral analytes (-)-cytidine and (-)-2-thiocytidine through the amplification of two receptors, (SS)-dimer and (RRRR)-tetramer. The deracemization phenomenon was investigated by laser polarimetry, mass-tagged pseudo-enantiomers in conjunction with electrospray ionization mass spectrometry, HPLC/UV-MS, UPLC/UV-MS, rapid-resolution LC-MS, collision-induced dissociation MS/MS, and numerical simulations. These data were consistent with a phenomenon where (SS)-dimer and (RRRR)-tetramer selectively bind the chiral analyte in preference to their enantiomeric counterparts, which ultimately causes them to be amplified and the library to become deracemized.
Chung et al. (Sat,) studied this question.