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Redox Reactions

Redox Reactions

Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Labeling DNA Probes

Labeling DNA Probes

DNA probes are fragments of DNA labeled with a reporter tag to enable their detection or purification. The resulting labeled DNA probes can then hybridize to target nucleic acid sequences through complementary base-pairing, and may be used to recover or identify these regions.
Radioisotopes, fluorophores, or small molecule binding partners like biotin or digoxigenin, are the most widely used reporter tags for labeling DNA probes. These labels can be attached to the probe DNA molecule via...

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

Alcohols from Carbonyl Compounds: Reduction

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

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Related Experiment Video

Updated: Jan 14, 2026

Sequence-specific Labeling of Nucleic Acids and Proteins with Methyltransferases and Cofactor Analogues

Sequence-specific Labeling of Nucleic Acids and Proteins with Methyltransferases and Cofactor Analogues

Published on: November 22, 2014

Two-step DNA redox labelling with borane cluster compounds.

Luděk Havran¹, Peter Šebest¹, Ece Zeynep Tüzun²

¹Institute of Biophysics of the Czech Academy of Sciences, Královopolská 135, 612 65 Brno, Czech Republic.

Bioelectrochemistry (Amsterdam, Netherlands)

|October 17, 2025

Summary

This summary is machine-generated.

Researchers developed a new method to label single-stranded DNA (ssDNA) with boron cluster compounds (BCCs). This advance in DNA redox labeling offers new possibilities for bioanalysis and diagnostics.

Keywords:

DNA redox labelling boron cluster compounds carbon electrodes electrochemistry

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Published on: March 20, 2018

Area of Science:

Biochemistry
Molecular Biology
Analytical Chemistry

Background:

DNA redox labeling is crucial for bioanalysis and diagnostics.
Boron cluster compounds (BCCs) offer a superior alternative to conventional labeling agents.

Purpose of the Study:

To introduce a novel two-step method for preparing single-stranded DNA (ssDNA) fragments labeled with BCC tags.
To expand the utility of DNA redox labeling for advanced applications.

Main Methods:

The study employed a two-step synthesis combining Huisgen azide-alkyne cycloaddition and terminal deoxynucleotidyl transferase tailing.
Ethynyl-decorated ssDNA was reacted with synthesized BCC-based azides.
Characterization involved polyacrylamide gel electrophoresis and electrochemical measurements.

Main Results:

Successful attachment of BCC-based azides to ethynyl-decorated ssDNA was achieved.
Electrochemical analysis confirmed the presence of BCC tags through distinct oxidation peaks.
The method yielded terminally BCC-labeled DNA oligonucleotides.

Conclusions:

The developed method provides a robust way to create BCC-labeled DNA.
This technique enhances the toolkit for DNA redox labeling.
It paves the way for novel bioanalytical and diagnostic tools.