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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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Published on: August 19, 2012

Boronic Acid Pairs for Sequential Bioconjugation.

Mary K Miller¹, Michael J Swierczynski¹, Yuxuan Ding¹

¹Department of Chemistry, Rice University, Houston, Texas 77005, United States.

Organic Letters

|July 2, 2021

Summary

This summary is machine-generated.

This study introduces two boronic acid compounds, 2-nitro-arylboronic acid (NAB) and (E)-alkenylboronic acid (EAB), for sequential cross-coupling. These novel boronic acids enable the creation of advanced bioconjugates and multifunctional probes.

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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

Published on: March 6, 2019

Area of Science:

Organic Chemistry
Bioconjugation Chemistry
Chemical Biology

Background:

Boronic acids are versatile in biological settings.
Tandem application of boronic acid structures offers potential for multifunctional probes.
Developing selective cross-coupling methods is crucial for bioconjugation.

Purpose of the Study:

To describe a pair of boronic acid functional groups for sequential cross-coupling.
To demonstrate the utility of these boronic acids in preparing complex bioconjugates.
To establish stepwise nickel- and copper-catalyzed processes for selective coupling.

Main Methods:

Utilizing 2-nitro-arylboronic acid (NAB) and (E)-alkenylboronic acid (EAB).
Employing sequential nickel- and copper-catalyzed cross-coupling reactions.
Applying selective coupling of NAB groups for bioconjugate synthesis.

Main Results:

Demonstrated sequential cross-coupling of NAB and EAB.
Successfully prepared stapled peptides using the selective coupling of NAB.
Synthesized protein-protein conjugates and other bioconjugates.
Established stepwise catalytic processes for controlled conjugation.

Conclusions:

The described boronic acid pair enables efficient and selective sequential cross-coupling.
This methodology provides new tools for creating multifunctional probes.
The selective coupling of NAB is particularly effective for synthesizing advanced bioconjugates like stapled peptides and protein conjugates.