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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 …
Charge-Mediated Recognition Of N-Terminal Tryptophan In Aqueous Solution By A Synthetic Host, Meghan Bush, Nicole Bouley, Adam Urbach
Charge-Mediated Recognition Of N-Terminal Tryptophan In Aqueous Solution By A Synthetic Host, Meghan Bush, Nicole Bouley, Adam Urbach
Adam R Urbach
The molecular recognition of peptides and proteins in aqueous solution by designed molecules remains an elusive goal with broad implications for basic biochemical research and for sensors and separations technologies. This paper describes the recognition of N-terminal tryptophan in aqueous solution by the synthetic host cucurbit[8]uril (Q8). Q8 is known to form 1:1:1 heteroternary complexes with methyl viologen (MV) and a second aromatic guest. Here, the complexes of Q8·MV with (i) the four natural aromatic α-amino acids, (ii) four singly charged tryptophan derivatives, and (iii) four tryptophan-containing tripeptides were characterized by isothermal titration calorimetry, mass spectrometry, and UV−visible, fluorescence, and …