Switching imidazole reactivity by dynamic control of tautomer state in an allosteric foldamer.

ABSTRACT: Molecular biology achieves control over complex reaction networks by means of molecular systems that translate a chemical input (such as ligand binding) into an orthogonal chemical output (such as acylation or phosphorylation). We present an artificial molecular translation device that converts a chemical input - the presence of chloride ions - into an unrelated chemical output: modulation of the reactivity of an imidazole moiety, both as a Brønsted base and as a nucleophile. The modulation of reactivity operates through the allosteric remote control of imidazole tautomer states. The reversible coordination of chloride to a urea binding site triggers a cascade of conformational changes in a chain of ethylene-bridged hydrogen-bonded ureas, switching the chain's global polarity, that in turn

SUBMITTER: Tilly DP 

PROVIDER: S-EPMC10167260 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature