期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 130, 期 35, 页码 11819-11827出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja803658n
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资金
- Defense Threat Reduction Agency (DTRA) [W911NF06-1-0169]
- Army Research Office [W911NF04D0004]
- Swiss National Science Foundation
- EPFL
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 (PPRR)-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.
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