Deracemization of a Dynamic Combinatorial Library Induced by (−)-Cytidine and (−)-2-Thiocytidine

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2008-09, Vol.130 (35), p.11819-11827
Main Authors: Chung, Mee-Kyung, Hebling, Christine M, Jorgenson, James W, Severin, Kay, Lee, Stephen J, Gagné, Michel R
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja803658n