Understanding enzyme catalysis by means of supramolecular artificial enzymes

Dong, Zeyuan; Zhu, Jun‐Yan; Luo, Quan

doi:10.1007/s11426-013-4871-3

Cited by 5 publications

(3 citation statements)

References 52 publications

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“…The use of supramolecular strategies to increase the rate of chemical transformations and control its selectivity was originally inspired by the mode of action of enzymes. − Enzymes are the most efficient biological catalysts . They bind their substrates in active sites by burying most of their surface.…”

Section: Introductionmentioning

confidence: 99%

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Hydration of Propargyl Esters Catalyzed by Gold(I) Complexes with Phosphoramidite Calix[4]pyrrole Cavitands as Ligands

Sierra,

Bulatov,

Aragay

et al. 2023

Inorg. Chem.

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We report the synthesis and characterization of two diastereomeric phosphoramidite calix [4]pyrrole cavitands and their corresponding gold(I) complexes, 2 in •Au(I)•Cl and 2 out •Au(I)•Cl, featuring the metal center directed inward and outward with respect to their aromatic cavity. We studied the catalytic activity of the complexes in the hydration of a series of propargyl esters as the benchmarking reaction. All substrates were equipped with a six-membered ring substituent either lacking or including a polar group featuring different hydrogen bond acceptor (HBA) capabilities. We designed the substrates with the polar group to form 1:1 inclusion complexes of different stabilities with the catalysts. In the case of 2 in •Au(I)•OTf, the 1:1 complex placed the alkynyl group of the bound substrate close to the metal center. We compared the obtained results with those of a model phosphoramidite gold(I) complex lacking a calix[4]pyrrole cavity. We found that for all catalysts, the presence of an increasingly polar HBA group in the substrate provoked a decrease in the hydration rate constants. We attributed this result to the competing coordination of the HBA group of the substrate for the Au(I) metal center of the catalysts.

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Section: Introductionmentioning

confidence: 99%

“…Reaction conditions:[3] = 10 mM, [catalyst] = 0.5 mM, rt, water saturated CD 2 Cl 2 . All reactions were performed at least in duplicate, and reported errors are standard deviations.…”

mentioning

confidence: 99%

Hydration of Propargyl Esters Catalyzed by Gold(I) Complexes with Phosphoramidite Calix[4]pyrrole Cavitands as Ligands

Sierra,

Bulatov,

Aragay

et al. 2023

Inorg. Chem.

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show abstract

“…To address this problem, a new strategy of supramolecular chemistry for enzymatic mimicking has recently been developed. 5,6,[12][13][14] It is well known that various weak supramolecular interactions play important roles in the recognition of substrates, stabilization of transition states, and enhancement of catalytic activities. 15,16 Based on the unique advantages of supramolecular chemistry, researchers can construct highly ordered nanostructures to mimic the characteristics of natural enzymes.…”

Section: Introductionmentioning

confidence: 99%