Azide-alkyne Cycloaddition

Azide-alkyne cycloaddition is a chemical reaction that joins an azide and an alkyne to form a stable 1,2,3-triazole ring, making it a valuable tool for selective molecular labeling in biology. In the copper-catalyzed version, copper(I) activates the alkyne and promotes bond formation with the azide; strain-promoted variants use strained cycloalkynes to avoid copper in living systems. These reactions support bioorthogonal tagging of proteins, glycans, lipids, and nucleic acids for fluorescence imaging, purification, and biochemical analysis. Their high selectivity and modularity enable studies of molecular localization, trafficking, and interactions, while copper-free approaches expand compatibility with live-cell and organismal experiments.

Azide-alkyne Cycloaddition - Related Videos

Research

JoVE Journal - Biochemistry

Efficient and Site-specific Antibody Labeling by Strain-promoted Azide-alkyne Cycloaddition

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Cited by 3 •

2016

Here, we present a protocol to site-specifically introduce chemical probes into an antibody fragment by genetically incorporating an azide-containing amino acid, and subsequently coupling the azide with a chemical probe by strain-promoted azide-alkyne cycloaddition (SPAAC).

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Cited by 1 •

2016

Here, we present a protocol to synthesize a complex organic compound comprised of three nonplanar polyaromatic units, assembled easily with reasonable yields.

Education

JoVE Core - Organic Chemistry

Nomenclature of Alkynes

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2025

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes: • IUPAC names • Common names IUPAC nomenclature The IUPAC naming system follows a systematic approach to deduce names of alkynes based on their chemical structure.

Cycloaddition Reactions: Overview

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2023

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition. The feasibility of cycloaddition reactions under thermal and photochemical conditions can be predicted using...

An Optimized Protocol for the Efficient Radiolabeling of Gold Nanoparticles by Using a 125I-labeled Azide Prosthetic Group

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Cited by 5 •

2016

A detailed procedure for the synthesis of a 125I-labeled azide and the radiolabeling of dibenzocyclooctyne (DBCO)-group-conjugated, 13-nm-sized gold nanoparticles using a copper-free click reaction is described.

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