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Dansyl amide

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Dansyl amide
Ball-and-stick model of the dansyl amide molecule
Names
Preferred IUPAC name
5-(Dimethylamino)naphthalene-1-sulfonamide
Other names
Dansyl amide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.413 Edit this at Wikidata
UNII
  • InChI=1S/C12H14N2O2S/c1-14(2)11-7-3-6-10-9(11)5-4-8-12(10)17(13,15)16/h3-8H,1-2H3,(H2,13,15,16) ☒N
    Key: TYNBFJJKZPTRKS-UHFFFAOYSA-N ☒N
  • InChI=1/C12H14N2O2S/c1-14(2)11-7-3-6-10-9(11)5-4-8-12(10)17(13,15)16/h3-8H,1-2H3,(H2,13,15,16)
    Key: TYNBFJJKZPTRKS-UHFFFAOYAD
  • O=S(=O)(c1cccc2c1cccc2N(C)C)N
Properties
C12H14N2O2S
Molar mass 250.31676
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dansyl amide is a fluorescent dye that forms in a reaction between dansyl chloride and ammonia. It is the simplest representative of the class of dansyl derivatized amines, which are widely used in biochemistry and chemistry as fluorescent labels.[1] The dansyl amide moiety is also called a dansyl group, and it can be introduced into amino acids or other amines in a reaction with dansyl chloride.[2] The dansyl group is highly fluorescent, and it has a very high Stokes shift. The excitation maximum (ca 350 nm) is essentially independent on the medium, whereas the emission maximum strongly depends on the solvent and varies from 520 to 550 nm.[3]

References

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  1. ^ Misra A, Tripathi S, Misra K (2000). "Fluorescent labelling of ribonucleosides at 2'-terminus; comparative fluorescence studies". Nucleic Acids Symp. Ser. 44 (44): 291–2. doi:10.1093/nass/44.1.291. PMID 12903383.
  2. ^ Tapuhi Y, Schmidt DE, Lindner W, Karger BL (July 1981). "Dansylation of amino acids for high-performance liquid chromatography analysis". Anal. Biochem. 115 (1): 123–9. doi:10.1016/0003-2697(81)90534-0. PMID 7304940.
  3. ^ Makoto Asano, Frangoise M.Winnik, Takashi Yamashita, and Kazuyuki Horief. Fluorescence Studies of Dansyl-Labeled Poly(iV-isopropylacrylamide)Gels and Polymers in Mixed Water/Methanol Solutions. Macromolecules, 1995, 28, 5861—5866.