| Revision as of 17:48, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 472095876 of page 3-Azidocoumarin for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 11:36, 13 January 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,042 edits Added s2cid. |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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| verifiedrevid = 449115625 |
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| verifiedrevid = 477218206 |
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| ImageFile = 3-Azidocoumarin.png |
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| ImageFile = 3-Azidocoumarin.png |
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| IUPACName = 3-Azido-2''H''-chromen-2-one |
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| PIN = 3-Azido-2''H''-1-benzopyran-2-one |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = <!-- blanked - oldvalue: 152711-55-2 --> |
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| CASNo = 152711-55-2 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|changed|??}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 24771406 |
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| ChemSpiderID = 24771406 |
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| PubChem = 53238503 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C9H5N3O2/c10-12-11-7-5-6-3-1-2-4-8(6)14-9(7)13/h1-5H |
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| StdInChI = 1S/C9H5N3O2/c10-12-11-7-5-6-3-1-2-4-8(6)14-9(7)13/h1-5H |
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| StdInChIKey = CYWSDGUZWKUALI-UHFFFAOYSA-N |
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| StdInChIKey = CYWSDGUZWKUALI-UHFFFAOYSA-N |
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| SMILES = O=C1C(N==)=CC2=CC=CC=C2O1}} |
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| SMILES = O=C1C(N==)=CC2=CC=CC=C2O1}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 9 | H = 6 | N = 3 | O = 2 |
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| C=9 | H=6 | N=3 | O=2 |
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| Appearance = Brown solid |
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| Appearance = Brown solid |
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| MeltingPt = 108-112 °C}} |
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| MeltingPtC = 108 to 112 |
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'''3-Azidocoumarin''' is an ] that is used in the area of ]. It is a derivative of ], a natural product and precursor for the widely used ]. Azidocoumarin has emerged as a widely applicable labeling agent in diverse biological systems. In particular, it participates in the aptly named '']'' with ].<ref>{{cite journal | author = R. A. Evans | year = 2007 | title = The Rise of Azide–Alkyne 1,3-Dipolar 'Click' Cycloaddition and its Application to Polymer Science and Surface Modification | journal = ] | doi = 10.1071/CH06457 | volume = 60 | issue = 6 | pages = 384}}</ref> Bioconjugation involves the labeling of certain cellular components and is applicable to fields such a ] and functional genomics with a detachable, fluorescent tag.<ref>Hermanson, G. T. ''Bioconjugate Techniques''; Academic Press: San Diego, 1996.</ref> |
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== Synthesis == |
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A common way to produce the 3-azidocoumarin is by condensation of ] and ] or nitroacetate.<ref name="Wang">{{cite journal | author = Q. Wang | year = 2004 | title = A Fluorogenic 1,3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes | journal = ] | doi = 10.1021/ol047955x | volume = 6 | issue = 24 | pages = 4603–4606| pmid = 15548086 |display-authors=etal}}</ref> The intermediate is trapped with ] to produce the 3-azidocoumarin. The isomeric 4-azidocoumarin (CAS# 42373-56-8) product can also be prepared from ] via the 4-chloro derivative, which reacts with sodium azide.<ref>{{cite journal | author = W. Stadlbauer | year = 1986 | title = Methoden zur Darstellung von 4-Azido-2(1"H")-chinolonen | journal = Monatshefte für Chemie | doi = 10.1007/BF00810876 | volume = 117 | issue = 11 | pages = 1305–1323| s2cid = 92478401 }}</ref> |
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== Uses == |
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This compound is used for bioconjugation. The target, which contains a ] functional group, is treated with the ] in the presence of a ] ]. The resulting ] 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.<ref name="Wang"/> Illustrative of this is the labeling of biological compounds such as the protein ].<ref>{{cite journal | author = T. Fekner | author2 = X. Li | author3 = M. M. Lee | author4 = M. K. Chan | name-list-style = amp | year = 2009 | title = A Pyrrolysine Analogue for Protein Click Chemistry | journal = ] | doi = 10.1002/anie.200805420 | volume = 48 | issue = 9 | pages = 1633–1635 | pmid=19156778}}</ref> 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. |
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== References == |
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{{reflist}} |
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{{DEFAULTSORT:Azidocoumarin, 3-}} |
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] |