Abstract
A rigid molecular clip comprising bisphosphonate binding sites and aromaticsidewalls forming an electron-rich cavity is able to distinguish between nucleosides andnucleotides in aqueous solution. Neutral nucleosides as well as antibiotics derived thereofare drawn into the unpolar interior of the cleft and lead to substantial upfield-shifts in the 1HNMR spectrum. Nucleoside drugs can therefore be detected with high selectivity in thepresence of their phosphorylated pendants or nucleic acids.
Highlights
Nucleoside drugs are of paramount importance in aids or cancer therapy due to their antiviral or antitumor activity
A rigid molecular clip comprising bisphosphonate binding sites and aromatic sidewalls forming an electron-rich cavity is able to distinguish between nucleosides and nucleotides in aqueous solution
Neutral nucleosides as well as antibiotics derived thereof are drawn into the unpolar interior of the cleft and lead to substantial upfield-shifts in the 1H NMR spectrum
Summary
Nucleoside drugs are of paramount importance in aids or cancer therapy due to their antiviral or antitumor activity. Abstract: A rigid molecular clip comprising bisphosphonate binding sites and aromatic sidewalls forming an electron-rich cavity is able to distinguish between nucleosides and nucleotides in aqueous solution. Klärner et al have created a large number of rigid molecular clips and tweezers, comprising an electron-rich cavity which is able to accomodate unpolar or cationic small guest molecules [5]. NMR titrations indicate inclusion in the clip cavity by substantial upfield shifts of all guest protons involved. At first glance it becomes evident, that only the neutral nucleoside candidates are bound by the clip, whereas the negatively charged nucleotides are rejected, except for AMP.
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