title: Deracemization of a dynamic combinatorial library induced by (-)-cytidine and (-)-2-thiocytidine.
abstract: 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.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
authors.forename: Mee-Kyung
authors.initials: MK
authors.lastname: Chung
authors.forename: Christine M
authors.initials: CM
authors.lastname: Hebling
authors.forename: James W
authors.initials: JW
authors.lastname: Jorgenson
authors.forename: Kay
authors.initials: K
authors.lastname: Severin
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Lee
authors.forename: Michel R
authors.initials: MR
authors.lastname: Gagné