Microelectrode Arrays, Dihydroxylation, and the Development of an Orthogonal Safety-Catch Linker

Yeh, Nai-Hua; Krueger, Ruby; Moeller, Kevin D.

doi:10.1021/acs.orglett.1c01675

Cited by 4 publications

(8 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Fluorescence microscopy. [39] Fluorescence images were carried out using a Nikon Eclipse E200 microscope and a Nikon D5000 camera with X-Cite Series 120 Q as the burner. Optical filters used with the Scheme 12.…”

Section: Methodsmentioning

confidence: 99%

“…The last task is done with the use of a "safety-catch" linker. [38,39] "Safety-catch" linkers contain both an ester moiety to attach a molecule to a solid support and a masked nucleophile that is positioned either five-or six-atoms away from the carbonyl of that ester. Unmasking of the nucleophile leads to a cyclization reaction with the nucleophile attacking the carbonyl in an addition step that is followed by an elimination step the removes the molecule from the solid support while forming either a lactone or lactam product depending on the nucleophile used.…”

Section: The Use Of Safety-catch Linkers and The Chan-lam Coupling Re...mentioning

confidence: 99%

“…A second generation approach took advantage of the oxidatively cleavable "safety-catch" linker strategy illustrated in Scheme 6. [39] The chemistry is illustrated in the context of the current studies with the linker placed on the array using a Cu(II)-mediated Chan-Lam coupling. The linker itself contains a monosubstituted olefin that is used to mask an alcohol nucleophile.…”

Section: The Use Of Safety-catch Linkers and The Chan-lam Coupling Re...mentioning

confidence: 99%

See 2 more Smart Citations

Microelectrode Arrays, Electrocatalysis, and the Need for Proper Characterization

Huang,

Krueger,

Moeller

2023

ChemElectroChem

Self Cite

View full text Add to dashboard Cite

Indirect electrochemical methods are a powerful tool for synthetic chemistry because they allow for the optimization of chemical selectivity in a reaction while maintaining the advantages of electrochemistry in terms of sustainability. Recently, we have found that such methods provide a handle for not only the synthesis of complex molecules, but also the construction of complex, addressable molecular surfaces. In this effort, the indirect electrochemical methods enable the placement or synthesis of molecules by any electrode or set of electrodes in a microelectrode array. The success of these surface‐based reactions are typically evaluated with the use of fluorescence labelling studies. However, these fluorescence‐based evaluations can be misleading. While they are excellent for determining that a reaction has occurred in a site‐selective fashion on an array, they do not provide information on whether that reaction is the one desired or how well it worked. We describe here how the use of a “safety‐catch” linker strategy allows for a more accurate assessment of reaction quality on an array, and then use that capability to illustrate how the use of transition metal mediated cross‐coupling reactions on an array prevent unwanted background reactions that can occur on a polymer‐coated electrode surface. The method enables a unique level of quality control for array‐based transformations.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: The Use Of Safety-catch Linkers and The Chan-lam Coupling Re...mentioning

confidence: 99%

Section: The Use Of Safety-catch Linkers and The Chan-lam Coupling Re...mentioning

confidence: 99%

See 1 more Smart Citation

Microelectrode Arrays, Electrocatalysis, and the Need for Proper Characterization

Huang,

Krueger,

Moeller

2023

ChemElectroChem

Self Cite

View full text Add to dashboard Cite

show abstract

“…For example, the chemistry in Scheme 22 illustrates how the Torii electrochemical adaptation of the Sharpless cis-hydroxylation reaction can be incorporated into a safety-catch linker in order to provide an orthogonal strategy for characterizing peptide derivatives synthesized on an array. 102 We hope by now it has become clear that strategies like the one illustrated in Scheme 22 capitalize on the interplay between two larger themes. One is that electrochemistry is an extremely versatile tool for making and recycling chemical reagents.…”

Section: ■ Future Directionsmentioning

confidence: 99%

“…We also know that we can use electrochemical methods to take advantage of many of the synthetic methods we already use in creative new ways to address synthesis in the array environment. For example, the chemistry in Scheme illustrates how the Torii electrochemical adaptation of the Sharpless cis-hydroxylation reaction can be incorporated into a safety-catch linker in order to provide an orthogonal strategy for characterizing peptide derivatives synthesized on an array …”

Section: Future Directionsmentioning

confidence: 99%

Capitalizing on Mediated Electrolyses for the Construction of Complex, Addressable Molecular Surfaces

Krueger

Moeller

2021

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

Synthetic organic chemists are beginning to exploit electrochemical methods in increasingly creative ways. This is leading to a surge in productivity that is only now starting to take advantage of the full-potential of electrochemistry for accessing new structures in novel, more efficient ways. In this perspective, we provide insight into the potential of electrochemistry as a synthetic tool gained through studies of both direct anodic oxidation reactions and more recent indirect methods, and highlight how the development of new electrochemical methods can expand the nature of synthetic problems our community can tackle.

show abstract

Lessons from an Array: Using an Electrode Surface to Control the Selectivity of a Solution‐Phase Chemical Reaction

2022

Self Cite

View full text Add to dashboard Cite

Electrochemistry offers a variety of novel means by which selectivity can be introduced into synthetic organic transformations. In the work reported, it is shown how methods used to confine chemical reactions to specific sites on a microelectrode array can also be used to confine a preparative reaction to the surface of an electrode inserted into a bulk reaction solution. In so doing, the surface of a modified electrode can be used to introduce new selectivity into a preparative reaction that is not observed in the absence of either the modified electrode surface or the effort to confine the reaction to that surface. The observed selectivity can be optimized in the same way that confinement is optimized on an array and is dependent on the nature of the functionalized surface.

show abstract

Microelectrode Arrays, Dihydroxylation, and the Development of an Orthogonal Safety-Catch Linker

Cited by 4 publications

References 30 publications

Microelectrode Arrays, Electrocatalysis, and the Need for Proper Characterization

Microelectrode Arrays, Electrocatalysis, and the Need for Proper Characterization

Capitalizing on Mediated Electrolyses for the Construction of Complex, Addressable Molecular Surfaces

Lessons from an Array: Using an Electrode Surface to Control the Selectivity of a Solution‐Phase Chemical Reaction

Contact Info

Product

Resources

About