3-Azidocoumarin
Names
Preferred IUPAC name
3-Azido-2H-1-benzopyran-2-one
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C9H5N3O2/c10-12-11-7-5-6-3-1-2-4-8(6)14-9(7)13/h1-5H checkY
    Key: CYWSDGUZWKUALI-UHFFFAOYSA-N checkY
  • O=C1C(N=[N+]=[N-])=CC2=CC=CC=C2O1
Properties
C9H6N3O2
Molar mass 188.166 g·mol−1
Appearance Brown solid
Melting point 108 to 112 °C (226 to 234 °F; 381 to 385 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

3-Azidocoumarin is an organic compound that is used in the area of bioconjugation. It is a derivative of coumarin, a natural product and precursor for the widely used Coumadin. Azidocoumarin has emerged as a widely applicable labeling agent in diverse biological systems. In particular, it participates in the aptly named click reaction with alkynes.[1] Bioconjugation involves the labeling of certain cellular components and is applicable to fields such a proteomics and functional genomics with a detachable, fluorescent tag.[2]

Synthesis

A common way to produce the 3-azidocoumarin is by condensation of salicylaldehyde and N-acetylglycine or nitroacetate.[3] 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 via the 4-chloro derivative, which reacts with sodium azide.[4]

Uses

This compound is used for bioconjugation. The target, which contains a terminal alkyne functional group, is treated with the organic azide 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.[3] Illustrative of this is the labeling of biological compounds such as the protein calmodulin.[5] 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

  1. ^ R. A. Evans (2007). "The Rise of Azide–Alkyne 1,3-Dipolar 'Click' Cycloaddition and its Application to Polymer Science and Surface Modification". Aust. J. Chem. 60 (6): 384. doi:10.1071/CH06457.
  2. ^ Hermanson, G. T. Bioconjugate Techniques; Academic Press: San Diego, 1996.
  3. ^ a b Q. Wang; et al. (2004). "A Fluorogenic 1,3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes". Org. Lett. 6 (24): 4603–4606. doi:10.1021/ol047955x. PMID 15548086.
  4. ^ W. Stadlbauer (1986). "Methoden zur Darstellung von 4-Azido-2(1"H")-chinolonen [1]". Monatshefte für Chemie. 117 (11): 1305–1323. doi:10.1007/BF00810876. S2CID 92478401.
  5. ^ T. Fekner; X. Li; M. M. Lee & M. K. Chan (2009). "A Pyrrolysine Analogue for Protein Click Chemistry". Angew. Chem. Int. Ed. 48 (9): 1633–1635. doi:10.1002/anie.200805420. PMID 19156778.
source: http://en.wikipedia.org/wiki/Azidocoumarin