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Physical Sciences and Mathematics Commons

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Chemistry

Selected Works

Adam R Urbach

2015

Equilibrium association constant

Articles 1 - 2 of 2

Full-Text Articles in Physical Sciences and Mathematics

Molecular Recognition Of Insulin By A Synthetic Receptor, Jordan Chinai, Alexander Taylor, Lisa Ryno, Nicholas Hargreaves, Christopher Morris, P Hart, Adam Urbach Nov 2015

Molecular Recognition Of Insulin By A Synthetic Receptor, Jordan Chinai, Alexander Taylor, Lisa Ryno, Nicholas Hargreaves, Christopher Morris, P Hart, Adam Urbach

Adam R Urbach

The discovery of molecules that bind tightly and selectively to desired proteins continues to drive innovation at the interface of chemistry and biology. This paper describes the binding of human insulin by the synthetic receptor cucurbit[7]uril (Q7) in vitro. Isothermal titration calorimetry and fluorescence spectroscopy experiments show that Q7 binds to insulin with an equilibrium association constant of 1.5 × 106 M−1 and with 50−100-fold selectivity versus proteins that are much larger but lack an N-terminal aromatic residue, and with >1000-fold selectivity versus an insulin variant lacking the N-terminal phenylalanine (Phe) residue. The crystal structure of the Q7·insulin complex shows …


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 Nov 2015

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 …