Switchable Catalysis Using Allosteric Effects

Schmittel, Michael

doi:10.1002/9783527832033.ch39

Supramolecular Catalysis 2021

DOI: 10.1002/9783527832033.ch39

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Switchable Catalysis Using Allosteric Effects

Michael Schmittel¹

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Cited by 2 publications

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“…For instance, ATP acts as an allosteric inhibitor of the phosphorylation of fructose by binding to phospho-fructokinase . To mimic allosteric modulation of enzyme activity, chemists have studied synthetic allosteric receptors and switchable catalysts, , but there are only few cases where the nanomechanical motion of a synthetic molecular machine is allosterically affected and one case in which additionally the organocatalytic efficiency is altered…”

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confidence: 99%

Parallel Allosteric Inhibition of Shuttling Motion and Catalysis in a Silver(I)-loaded [2]Rotaxane

et al. 2022

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A dynamic silver(I)-loaded [2]rotaxane shuttle (k 298 = 135 kHz) was converted allosterically into a conformationally restricted [2]rotaxane due to the creation of a bulky imine in the center of the axle component. Only the dynamic silver(I)-loaded [2]rotaxane was able to catalyze a 6-endo-cyclization reaction, whereas the static one was catalytically quiet. The mechanism of catalyst deactivation was elucidated.

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Parallel Allosteric Inhibition of Shuttling Motion and Catalysis in a Silver(I)-loaded [2]Rotaxane

et al. 2022

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

Tilly,

Heeb,

Webb

et al. 2023

Nat Commun

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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 modulates the tautomeric equilibrium of a distal imidazole, and hence its reactivity. Switching reactivities of active sites by dynamically controlling their tautomer states is an untapped strategy for building functional molecular devices with allosteric enzyme-like properties.

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Switchable Catalysis Using Allosteric Effects

Cited by 2 publications

References 42 publications

Parallel Allosteric Inhibition of Shuttling Motion and Catalysis in a Silver(I)-loaded [2]Rotaxane

Parallel Allosteric Inhibition of Shuttling Motion and Catalysis in a Silver(I)-loaded [2]Rotaxane

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

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