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Related Concept Videos

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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.
Labeling DNA Probes03:31

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 Hydroboration02:36

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.
Hydrolysis01:15

Hydrolysis

Overview
Hydrolysis is a chemical reaction in which the addition of water breaks down a polymer into its simpler monomer units. For example, peptides break into amino acids, carbohydrates into simple sugars, and DNA into nucleotides. Enzymes often facilitate these processes.
Hydrolysis Reverses Dehydration Synthesis
Complex carbohydrates can be broken down by breaking the bonds between individual sugar units. The reaction breaks a glycosidic bond as water is added to the compound. The...
Hydroboration-Oxidation of Alkenes03:08

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.

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Updated: Jun 27, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Click and release through bioorthogonal hydroamination.

Yiming Guo1, Tyler J Brown1, Justin Kim1

  • 1School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA, United States.

Methods in Enzymology
|June 25, 2026
PubMed
Summary
This summary is machine-generated.

This study introduces a novel click-and-release strategy using bioorthogonal chemistry for flexible biomolecule modification. It enables controlled sequential reactions and bond cleavage for enhanced operational flexibility in biological applications.

Keywords:
Bioorthogonal chemistryClick-and-releaseDiboron-mediated reductionHydroaminationProtein modificationReversible protein labeling

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Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Biotechnology

Background:

  • Click chemistry and bioorthogonal reactions are vital for modifying biological systems.
  • Current methods often focus on conjugation or dissociation, with challenges in coordinating multiple reactions.
  • Controlled manipulation of biomolecules requires advanced chemical strategies.

Purpose of the Study:

  • To develop a versatile click-and-release strategy for complex biological modifications.
  • To enable modular and controlled sequential chemical transformations on biomolecules.
  • To enhance operational flexibility in bioorthogonal chemistry applications.

Main Methods:

  • Development of a click-and-release system utilizing bioorthogonal hydroamination.
  • Generation of discrete, isolable conjugates as intermediates.
  • Demonstration of independent induction of bond cleavage after initial conjugation.

Main Results:

  • A novel bioorthogonal hydroamination reaction was successfully employed for a click-and-release strategy.
  • Discrete conjugates were formed, allowing for subsequent chemical or biochemical modifications.
  • Independent bond cleavage was achieved, demonstrating the strategy's flexibility.

Conclusions:

  • The developed click-and-release strategy offers enhanced operational flexibility for complex biological manipulations.
  • This approach facilitates controlled, sequential chemical transformations in a biological context.
  • The method provides a modular platform for advanced bioorthogonal chemistry applications.