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Related Concept Videos

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.
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.
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...
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...
Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

Nucleophilic Addition to the Carbonyl Group: General Mechanism

The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of the incoming nucleophile, the reaction occurs via different mechanistic pathways.
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the π bonding...

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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

"Chemical ligation": a versatile method for nucleoside modification with boron clusters.

Błazej A Wojtczak1, Agnieszka Andrysiak, Bohumír Grüner

  • 1Institute of Medical Biology, Laboratory of Molecular Virology and Biological Chemistry, Polish Academy of Sciences, 106 Lodowa St. 93-232 Lodz, Poland.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 24, 2008
PubMed
Summary

Researchers developed a new method for synthesizing boron-cluster-modified nucleosides using "chemical ligation." This approach enables the creation of diverse nucleoside conjugates for various applications.

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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

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Last Updated: Jun 28, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
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Nucleoside Triphosphates - From Synthesis to Biochemical Characterization

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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
08:46

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Boron Chemistry

Background:

  • Nucleoside conjugates are important in various fields, including medicine and materials science.
  • Developing efficient synthetic routes for complex nucleoside derivatives is crucial.
  • Boron clusters offer unique properties for applications in drug delivery and imaging.

Purpose of the Study:

  • To establish a general synthetic strategy for nucleoside conjugates incorporating carborane and metallocarborane complexes.
  • To utilize Huisgen 1,3-dipolar cycloaddition for efficient conjugation.
  • To create diverse libraries of boron-cluster-modified nucleosides.

Main Methods:

  • Synthesis of boron-cluster donors with terminal azide or ethynyl groups via ring-opening reactions.
  • Preparation of analogous derivatives with terminal sulfhydryl groups.
  • Utilizing nucleosides with functionalized spacers as boron-cluster acceptors in cycloaddition reactions.

Main Results:

  • Successful synthesis of boron-cluster donors and acceptors.
  • Demonstration of the Huisgen 1,3-dipolar cycloaddition for creating carborane and metallocarborane nucleoside conjugates.
  • Generation of diverse libraries of modified nucleosides.

Conclusions:

  • The described methodology offers a convenient and versatile approach for synthesizing boron-cluster-modified nucleosides.
  • This method facilitates the creation of libraries for exploring new applications.
  • The developed strategy is applicable to both carborane and metallocarborane complexes.