Dansyl chloride

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Dansyl chloride[1]
IUPAC name 5-(dimethylamino)naphthalene-1-sulfonyl chloride
Identifiers
CAS number [605-65-2]
RTECS number QK3688000
Properties
Molecular formula C12H12ClNO2S
Molar mass 269.75 g/mol
Melting point

70 °C, 343 K, 158 °F
Hazards
EU classification Corrosive (C)
R-phrases R34
S-phrases S26 S36/37/39 S45
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Dansyl chloride or 5-(dimethylamino)naphthalene-1-sulfonyl chloride is a reagent that reacts with primary amino groups in both aliphatic and aromatic amines to produce stable blue- or blue-green–fluorescent sulfonamide adducts. Dansyl chloride is widely used in protein sequencing and amino acid analysis.[2][3]

In addition, these adducts are, in general, good acceptors for fluorescence resonance energy transfer from the amino acid tryptophan, allowing this labeling technique to be used in investigating protein flexibility. The fluorescence of these sulfonamide adducts can be enhanced by adding cycloheptaamylose.[4] It is important to note that dansyl chloride is unstable in dimethyl sulfoxide, which should never be used to prepare solutions of the reagent.

[edit] References

  1. ^ MSDS. Sigma-Aldrich. Retrieved on 2007-12-02.
  2. ^ Walker JM (1994). "The dansyl method for identifying N-terminal amino acids". Methods Mol. Biol. 32: 321–8. doi:10.1385/0-89603-268-X:321. PMID 7951732. 
  3. ^ Walker JM (1994). "The Dansyl-Edman method for peptide sequencing". Methods Mol. Biol. 32: 329–34. doi:10.1385/0-89603-268-X:329. PMID 7951733. 
  4. ^ Kinoshita T, Iinuma F, Tsuji A (1974). "Microanalysis of proteins and peptides. I. Enhancement of the fluorescence intensity of dansyl amino acids and dansyl proteins in aqueous media and its application to assay of amino acids and proteins". Chem. Pharm. Bull. 22 (10): 2413–20. PMID 4468087. 
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