Abstract
The long-range communication of information, exemplified by signal transduction through membrane-bound receptors, is a central biochemical function. Reversible binding of a messenger ligand induces a local conformational change that is relayed through the receptor, inducing a chemical effect typically several nanometres from the binding site. We report a synthetic receptor mimic that transmits structural information from a boron-based ligand binding site to a spectroscopic reporter located more than 2 nm away. Reversible binding of a diol ligand to the N-terminal binding site induces a screw-sense preference in a helical oligo(aminoisobutyric acid) foldamer, which is relayed to a reporter group at the remote C-terminus, communicating information about the structure and stereochemistry of the ligand. The reversible nature of boronate esterification was exploited to switch the receptor sequentially between left- and right-handed helices, while the exquisite conformational sensitivity of the helical relay allowed the reporter to differentiate even between purine and pyrimidine nucleosides as ligands.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Boronic Acids / chemistry
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Ligands
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Magnetic Resonance Spectroscopy
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Molecular Conformation
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Protein Binding
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Receptors, Purinergic / chemistry*
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Ribonucleosides / chemistry
Substances
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Boronic Acids
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Ligands
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Receptors, Purinergic
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Ribonucleosides
Associated data
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PubChem-Substance/163831253
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PubChem-Substance/163831254
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PubChem-Substance/163831255
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PubChem-Substance/163831256
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PubChem-Substance/163831270
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PubChem-Substance/163831271
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PubChem-Substance/163831272
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PubChem-Substance/163831273
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PubChem-Substance/163831274
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PubChem-Substance/163831275
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PubChem-Substance/163831299