3-Azidocoumarin is an
organic compound that is used in the area of
bioconjugation
Bioconjugation is a chemical strategy to form a stable covalent link between two molecules, at least one of which is a biomolecule.
Function
Recent advances in the understanding of biomolecules enabled their application to numerous fields like ...
. It is a derivative of
coumarin, a natural product and precursor for the widely used
Coumadin
Warfarin, sold under the brand name Coumadin among others, is a medication that is used as an anticoagulant (blood thinner). It is commonly used to prevent blood clots such as deep vein thrombosis and pulmonary embolism, and to prevent strok ...
. Azidocoumarin has emerged as a widely applicable labeling agent in diverse biological systems. In particular, it participates in the aptly named ''
click reaction
In chemical synthesis, click chemistry is a class of biocompatible small molecule reactions commonly used in bioconjugation, allowing the joining of substrates of choice with specific biomolecules. Click chemistry is not a single specific reaction, ...
'' with
alkynes. Bioconjugation involves the labeling of certain cellular components and is applicable to fields such a
proteomics
Proteomics is the large-scale study of proteins. Proteins are vital parts of living organisms, with many functions such as the formation of structural fibers of muscle tissue, enzymatic digestion of food, or synthesis and replication of DNA. In ...
and functional genomics with a detachable, fluorescent tag.
Synthesis
A common way to produce the 3-azidocoumarin is by condensation of
salicylaldehyde and
''N''-acetylglycine or nitroacetate.
The intermediate is trapped with
sodium azide to produce the 3-azidocoumarin. The isomeric 4-azidocoumarin (CAS# 42373-56-8) product can also be prepared from
4-hydroxycoumarin
4-Hydroxycoumarin is a coumarin derivative with a hydroxy group at the 4-position.
Occurrence
4-Hydroxycoumarin is an important fungal metabolite from the precursor coumarin, and its production leads to further fermentative production of the nat ...
via the 4-chloro derivative, which reacts with sodium azide.
Uses
This compound is used for bioconjugation. The target, which contains a
terminal alkyne
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Acetylene
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Propyne
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1-Butyne
In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no ...
functional group, is treated with the
organic azide
An organic azide is an organic compound that contains an azide (–) functional group. Because of the hazards associated with their use, few azides are used commercially although they exhibit interesting reactivity for researchers. Low molecular w ...
in the presence of a
Cu(I) catalyst. The resulting
1,2,3-triazole is fluorescent. The coumarin backbone is chosen to be used as the profluorophore due to its small size, biocompatibility, and its ability to be easily manipulated synthetically.
Illustrative of this is the labeling of biological compounds such as the protein
calmodulin
Calmodulin (CaM) (an abbreviation for calcium-modulated protein) is a multifunctional intermediate calcium-binding messenger protein expressed in all eukaryotic cells. It is an intracellular target of the secondary messenger Ca2+, and the bind ...
.
Neither the azidocoumarin nor the alkyne substrate fluoresce. Azidocoumarin is also inert in biological systems and insensitive to pH and solvent. A variety of azidocoumarin compounds have been evaluated.
References
{{DEFAULTSORT:Azidocoumarin, 3-
Organoazides
Coumarins
Reagents for biochemistry