DNA-Scaffolded Synergistic Catalysis

Pimentel, Edward B.; Peters-Clarke, Trenton M.; Coon, Joshua J.; Martell, Jeffrey D.

doi:10.1021/jacs.1c10757

Cited by 16 publications

(23 citation statements)

References 92 publications

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“…C. The remarkable influence of effective molarity, as achieved by DNA-scaffolding on rate particularly as one dilutes the individual components particularly at low loading. Panel C reproduced with permission from ref . Copyright 2021 American Chemical Society.…”

Section: Discussionmentioning

confidence: 93%

“…Finally, the ability of nucleic acids to position candidate catalytic components at a potential reaction center has the possibility to really open up a much higher throughput exploration of combinatorial catalysis space. The potential here is perhaps best illustrated by a recent disclosure from Pimentel and Martell in which DNA scaffolding technology was used to demonstrate just how important effective molarity can be for the exploration of synergistic catalysis. As a platform reaction, the Wisconsin team utilized the Stahl oxidation , of alcohols to aldehydes.…”

Section: Discussionmentioning

confidence: 99%

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Biomacromolecule-Assisted Screening for Reaction Discovery and Catalyst Optimization

et al. 2022

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Reaction discovery and catalyst screening lie at the heart of synthetic organic chemistry. While there are efforts at de novo catalyst design using computation/artificial intelligence, at its core, synthetic chemistry is an experimental science. This review overviews biomacromolecule-assisted screening methods and the follow-on elaboration of chemistry so discovered. All three types of biomacromolecules discussed�enzymes, antibodies, and nucleic acids�have been used as "sensors" to provide a readout on product chirality exploiting their native chirality. Enzymatic sensing methods yield both UV-spectrophotometric and visible, colorimetric readouts. Antibody sensors provide direct fluorescent readout upon analyte binding in some cases or provide for cat-ELISA (Enzyme-Linked ImmunoSorbent Assay)-type readouts. DNA biomacromolecule-assisted screening allows for templation to facilitate reaction discovery, driving bimolecular reactions into a pseudounimolecular format. In addition, the ability to use DNA-encoded libraries permits the barcoding of reactants. All three types of biomacromolecule-based screens afford high sensitivity and selectivity. Among the chemical transformations discovered by enzymatic screening methods are the first Ni(0)-mediated asymmetric allylic amination and a new thiocyanopalladation/carbocyclization transformation in which both C−SCN and C−C bonds are fashioned sequentially. Cat-ELISA screening has identified new classes of sydnone-alkyne cycloadditions, and DNA-encoded screening has been exploited to uncover interesting oxidative Pd-mediated amido-alkyne/alkene coupling reactions.

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Section: Discussionmentioning

confidence: 93%

Section: Discussionmentioning

confidence: 99%

Biomacromolecule-Assisted Screening for Reaction Discovery and Catalyst Optimization

et al. 2022

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“…[ 95 ] Finally, the reversible nature opens the door to designed switchable systems, allowing a given device or material to change its properties on demand. [ 96 ] Such systems could form the basis of adaptive materials, organic semi‐conductors and logic gates, biosensors, or organic soft robotics.…”

Section: Discussionmentioning

confidence: 99%

Peptide‐assistedsupramolecular polymerization of the anionic porphyrinmeso‐tetra(4‐sulfonatophenyl)porphine

et al. 2022

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Electronics made from biological materials are desirable for use in medical devices, biosensors, and soft robotics because they have properties inaccessible to current inorganic technologies. Here, a series of cationic peptides were developed to selfassemble with the anionic porphyrin meso-tetra(4-sulfonatophenyl)porphine (TPPS 4 ) into supramolecular light-harvesting wires known as J-aggregates were developed. In addition to quantifying the binding events between each peptide and TPPS 4 , we found co-incubation with mixed peptides allowed TPPS 4 to bridge two different peptides at their terminal porphyrin-binding regions. The J-aggregates formed on macroscopic scale in near quantitative yield within $3 h and readily interconverted with the soluble monomers upon cycling the pH; to our knowledge, this is the first report of a peptide-porphyrin system with such properties. This work has practical and conceptual relevance to the development of new bioelectronic materials.

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“…A very rare example is that of a synergistic catalytic system based on a DNA scaffold. Martell and co‐workers reported a DNA‐scaffolded synergistic catalyst system, in which both catalytic sites were artificially introduced [63] . In this case, the oxidation of the β‐naphthalene methanol by O 2 was promoted synergistically with the assistance of the Cu catalytic site and the radical initiator site (Scheme 17).…”

Section: Dual Catalysis With Biomacromoleculesmentioning

confidence: 99%

Dual Catalysis in Organic Synthesis: Current Challenges and New Trends

2022

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Dual catalysis is one of the most powerful strategies for the development of chemical reactions in organic synthesis. This strategy can be divided into cooperative catalysis, relay catalysis, and sequential catalysis according to the actual mode of operation and the communication between the catalysts. In recent years, such strategy has been applied in a large number of studies since it has the advantages of: 1) increasing reactivity and enabling challenging transformations; 2) offering a powerful way of controlling the stereoselectivity of asymmetric reactions, which is challenging for traditional catalytic systems; 3) catalyze the stereodivergent synthesis of molecules bearing one or more stereocenters from the same starting materials. This Perspective, which intends to introduce the reader to EurJOC special collection on Dual Catalysis , aims to summarize and introduce the different categories of dual catalysis and demonstrate their benefits in constructing new chemical bonds in a selective manner. Finally, current challenges and new trends in dual catalysis will be also presented.

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DNA-Scaffolded Synergistic Catalysis

Cited by 16 publications

References 92 publications

Biomacromolecule-Assisted Screening for Reaction Discovery and Catalyst Optimization

Biomacromolecule-Assisted Screening for Reaction Discovery and Catalyst Optimization

Peptide‐assistedsupramolecular polymerization of the anionic porphyrinmeso‐tetra(4‐sulfonatophenyl)porphine

Dual Catalysis in Organic Synthesis: Current Challenges and New Trends

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