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Scope Of Amino Acid Recognition By Cucurbit[8]Uril, Preetika Rajgariah, Adam Urbach
Scope Of Amino Acid Recognition By Cucurbit[8]Uril, Preetika Rajgariah, Adam Urbach
Adam R Urbach
This paper describes the molecular recognition of amino acids by cucurbit[8]uril (Q8) and by the 1:1 complex between Q8 and methyl viologen (MV) in purely aqueous solution. These hosts are known to bind aromatic peptides with high affinity and sequence specificity, but prior work has focused on only a small subset of amino acids. In an effort to elucidate the scope and limitations of amino acid recognition by Q8 and Q8•MV, a comprehensive examination of the 20 genetically encoded amino acids was carried out by 1H NMR spectroscopy and isothermal titration calorimetry. We find that both Q8 and Q8•MV …
Benzobis(Imidazolium)–Cucurbit[8]Uril Complexes For Binding And Sensing Aromatic Compounds In Aqueous Solution, Frank Biedermann, Urs Rauwald, Monika Cziferszky, Kyle Williams, Lauren Gann, Bi Guo, Adam Urbach, Christopher Bielawski, Oren Scherman
Benzobis(Imidazolium)–Cucurbit[8]Uril Complexes For Binding And Sensing Aromatic Compounds In Aqueous Solution, Frank Biedermann, Urs Rauwald, Monika Cziferszky, Kyle Williams, Lauren Gann, Bi Guo, Adam Urbach, Christopher Bielawski, Oren Scherman
Adam R Urbach
The utilities of benzobis(imidazolium) salts (BBIs) as stable and fluorescent components of supramolecular assemblies involving the macrocyclic host, cucurbit[8]uril (CB[8]), are described. CB[8] has the unusual ability to bind tightly and selectively to two different guests in aqueous media, typically methyl viologen (MV) as the first guest, followed by an indole, naphthalene, or catechol-containing second guest. Based on similar size, shape, and charge, tetramethyl benzobis(imidazolium) (MBBI) was identified as a potential alternative to MV that would increase the repertoire of guests for cucurbit[8]uril. Isothermal titration calorimetry (ITC) studies showed that MBBI binds to CB[8] in a 1:1 ratio with an …