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

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• 作者：Mee-Kyung Chung ; Christine M. Hebling ; James W. Jorgenson ; Kay Severin ; Stephen J. Lee ; Michel R. Gagné
• 刊名：Journal of the American Chemical Society
• 出版年：2008
• 出版时间：9/3/08
• 年：2008
• 卷：130
• 期：35
• 页码：11819-11827
• 全文大小：540K
• 年卷期：v.130,no.35(9/3/08)
• ISSN：1520-5126

文摘

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.