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Nanomolar Binding Of Peptides Containing Noncanonical Amino Acids By A Synthetic Receptor, Leigh Logsdon, Christopher Schardon, Vijayakumar Ramalingam, Sharon Kwee, Adam Urbach
Nanomolar Binding Of Peptides Containing Noncanonical Amino Acids By A Synthetic Receptor, Leigh Logsdon, Christopher Schardon, Vijayakumar Ramalingam, Sharon Kwee, Adam Urbach
Adam R Urbach
This paper describes the molecular recognition of phenylalanine derivatives and their peptides by the synthetic receptor cucurbit[7]uril (Q7). The 4-tert-butyl and 4-aminomethyl derivatives of phenylalanine (tBuPhe and AMPhe) were identified from a screen to have 20–30-fold higher affinity than phenylalanine for Q7. Placement of these residues at the N-terminus of model tripeptides (X-Gly-Gly), resulted in no change in affinity for tBuPhe-Gly-Gly, but a remarkable 500-fold increase in affinity for AMPhe-Gly-Gly, which bound to Q7 with an equilibrium dissociation constant (Kd) value of 0.95 nM in neutral phosphate buffer. Structure–activity studies revealed that three functional groups work in a positively cooperative …
Solid-Phase Synthesis Of Peptide−Viologen Conjugates, Joseph Reczek, Elisa Rebolini, Adam Urbach
Solid-Phase Synthesis Of Peptide−Viologen Conjugates, Joseph Reczek, Elisa Rebolini, Adam Urbach
Adam R Urbach
This paper presents a robust method for the conjugation of viologens to peptides using an amide coupling strategy that is compatible with standard Fmoc solid-phase peptide synthesis. Methodology is presented for monitoring the milligram scale process quantitatively by UV spectroscopy. This chemistry enables the synthesis of a broad range of asymmetric viologens in high yield at room temperature and is compatible with a wide range of functional groups, including amine, guanidinyl, thiol, carboxylic acid, phenol, and indole.