Controllable stereoinversion in DNA-catalyzed olefin cyclopropanation <i>via</i> cofactor modification

Hao, Jingya; Miao, Wenhui; Lü, Shouqin; Cheng, Yu; Jia, Guifang; Li, Can

doi:10.1039/d1sc00755f

Cited by 14 publications

(6 citation statements)

References 53 publications

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“…Consequently, the topology at these sites is critical when treating the structure as a chiral ligand, as this is the environment in which the reaction occurs. G4 structures has also been designed for artificial metalloenzymes based on DNA metalloenzymes. , Recently, Li et al developed a series of reactions involving G4 metalloenzyme catalysis, − employing G4 and Fe porphyrin as promising biocatalysts for olefin cyclopropanation (Figure A) …”

Section: General Character and Applications Of G-quadruplexmentioning

confidence: 99%

Recent Developments in G-Quadruplex Binding Ligands and Specific Beacons on Smart Fluorescent Sensor for Targeting Metal Ions and Biological Analytes

et al. 2022

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The G-quadruplex structure is crucial in several biological processes, including DNA replication, transcription, and genomic maintenance. G-quadruplex-based fluorescent probes have recently gained popularity because of their ease of use, low cost, excellent selectivity, and sensitivity. This review summarizes the latest applications of G-quadruplex structures as detectors of genome-wide, enantioselective catalysts, disease therapeutics, promising drug targets, and smart fluorescence probes. In every section, sensing of Gquadruplex and employing G4 for the detection of other analytes were introduced, respectively. Since the discovery of the G-quadruplex structure, several studies have been conducted to investigate its conformations, biological potential, stability, reactivity, selectivity for chemical modification, and optical properties. The formation mechanism and advancements for detecting different metal ions

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Section: General Character and Applications Of G-quadruplexmentioning

confidence: 99%

Recent Developments in G-Quadruplex Binding Ligands and Specific Beacons on Smart Fluorescent Sensor for Targeting Metal Ions and Biological Analytes

et al. 2022

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“…The recent advances in supramolecular DNA hybrid catalysts clearly demonstrated the capacity of DNA as a chiral source and support the use of DNA-based biocatalysts in a much broader spectrum of reactions. Despite the ongoing efforts to gain mechanistic insight by inferring the active site from spectroscopic analysis, [37,47] there were still issues that could not be answered clearly. For instance, it was difficult to accurately represent the exact position and the binding mode of metalligand complexes on DNA.…”

Section: Modular Dna Hybrid Catalysts By Direct Incorporation Of Meta...mentioning

confidence: 99%

“…The remarkable catalytic ability of G4 scaffolds combined with iron-porphyrins (Fe-TMPyP4) has been reported. [36,37] Inspired by the first example of G4 DNA-based hybrid catalysts for enantioselective cyclopropanation, [38] Li and colleagues improved the catalyst performance by further optimization. The diastereomeric cyclopropanes have been synthesized from styrene derivatives 4a-c and ethyl diazoacetate (EDA, 5a-c) (Scheme 2).…”

Section: The Advent Of Dna-based Hybrid Catalysts: Supramolecular-ass...mentioning

confidence: 99%

Harnessing DNA as a Designable Scaffold for Asymmetric Catalysis: Recent Advances and Future Perspectives

Yum

Sugiyama

Park

2022

The Chemical Record

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Since the first report of DNAzyme by in vitro selection in 1994, catalytic DNA has investigated extensively, and their application has expanded continually in virtue of rapid advances in molecular biology and biotechnology. Nowadays, DNA is in the second prime time by way of DNA-based hybrid catalysts and DNA metalloenzymes in which helical chirality of DNA serves to asymmetric catalysis. DNA-based hybrid catalysts are attractive system to respond the demand of the times to pursuit green and sustainable society beyond traditional catalytic systems that value reaction efficiency. Herein, we highlight the recent advances and perspective of DNA-based hybrid catalysts with various aspects of DNA as a versatile scaffold for asymmetric synthesis. We hope that scientists in a variety of fields will be encouraged to join and promote remarkable evolution of this interesting research.

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“…[14,15] Indeed, it was shown that the hybrid formed with a G-4 and the natural peroxidase cofactor hemin (iron(III) chloroprotoporphyrin IX), with the porphyrin group stacked on top of apical quartets, was able to mimic the natural peroxidase upon addition of H 2 O 2 . [16][17][18] It was also found that this combination could catalyze oxygen transfer reactions but without any enantioselectivity [19] (whereas it is able to catalyze asymmetric cyclopropanation reactions [20,21] ).…”

Section: Introductionmentioning

confidence: 99%

Use of Constrained G‐Quadruplexes for Enantioselective Sulfoxidation Site Mapping

Colas,

Ménage,

Marchi‐Delapierre

et al. 2023

ChemCatChem

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Catalysis using G‐quadruplexes (G‐4) has shown promise as a way to perform asymmetric sulfoxidation of thioanisole derivatives. However, despite the relative simplicity of G‐4, the mechanism of chiral control of sulfoxidation is still unknown, mainly because G‐4 can adopt different topologies. To better understand the mechanism of G‐4‐catalyzed sulfoxidation, we chemically constrained G‐4 into a unique topology. We show that either sulfoxidation can occur at the outer tetrads or at the grooves of G‐4 and that different enantiomers can be generated depending on the region where catalysis occurs. Thus, thanks to our G‐4 mimics, we can unravel the enantioselective control of the sulfoxidation reaction.

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Controllable stereoinversion in DNA-catalyzed olefin cyclopropanation via cofactor modification

Abstract: Cofactor modification in a DNA-catalyzed olefin cyclopropanation reaction enables controllable stereoinversion and achieves enantioselectivities of up to +91% and −72% eetrans.

Cited by 14 publications

References 53 publications

Recent Developments in G-Quadruplex Binding Ligands and Specific Beacons on Smart Fluorescent Sensor for Targeting Metal Ions and Biological Analytes

Recent Developments in G-Quadruplex Binding Ligands and Specific Beacons on Smart Fluorescent Sensor for Targeting Metal Ions and Biological Analytes

Harnessing DNA as a Designable Scaffold for Asymmetric Catalysis: Recent Advances and Future Perspectives

Use of Constrained G‐Quadruplexes for Enantioselective Sulfoxidation Site Mapping

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