Dansyl chloride

Structural formula
General
Surname	Dansyl chloride
other names	5- (Dimethylamino) naphthalene-1-sulfonyl chloride ( IUPAC )
Molecular formula	C 12 H 12 ClNO 2 S
Brief description	yellow odorless solid
External identifiers / databases
CAS number 605-65-2 EC number 210-092-6 ECHA InfoCard 100.009.175 PubChem 11801 ChemSpider 11308 Wikidata Q409512
properties
Molar mass	269,75 g · mol -1
Physical state	firmly
Melting point	69-71 ° C
solubility	heavy in water (10 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 314 P: 280-305 + 351 + 338-310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dansyl chloride , chemically: 5- (dimethylamino) naphthalene-1-sulfonyl chloride , is used as a reagent for primary aliphatic and aromatic amino groups. With these it forms stable blue- or blue-green fluorescent sulfonamides. Dansyl chloride is a widely used tool in the end grouping of peptides and in amino acid analysis . It was first synthesized by Gregorio Weber in the early 1950s.

Application principle in the end group determination of peptides

Dansyl chloride reacts with terminal amino groups in peptides and forms adducts with high hydrolytic stability. The subsequent hydrolysis of the peptide adducts therefore leads to the cleavage of the peptide bonds, the adduct of the terminal amino acid and dansyl chloride being retained and being able to be characterized by chromatography .

Application in the flexibility study of proteins

The sulfonamides formed with amino acids are generally good acceptors for fluorescence resonance energy transfer (FRET) in combination with the amino acid tryptophan , which makes labeling with dansyl chloride a suitable means for studying the flexibility of proteins . The addition of β-cyclodextrin (cycloheptaamylose) increases the resonance of the sulfonamide adducts.

Chemical properties

Dansyl chloride is unstable in dimethyl sulfoxide (DMSO), which is therefore not suitable as a solvent for the reagent.

Individual evidence

1. ↑ ^{a b c} Entry on 5-dimethylaminonaphthalene-1-sulfonyl chloride in the GESTIS substance database of the IFA , accessed on February 10, 2017(JavaScript required) .
2. ↑ ^{a b} Data sheet dansyl chloride (PDF) from Carl Roth , accessed on March 7, 2010.
3. ^ John M. Walker: The Dansyl Method for Identifying N-Terminal Amino Acids. In: Bryan John Smith (Ed.): Protein Sequencing Protocols (= Methods in Molecular Biology. Volume 32) Humana Press, 1994, ISBN 0-89603-268-X , pp. 321-328, doi : 10.1385 / 0-89603 -268-X: 321 .
4. ↑ John M. Walker: The Dansyl-Edman method for peptide sequencing. In: Bryan John Smith (Ed.): Protein Sequencing Protocols (= Methods in Molecular Biology. Volume 32) Humana Press, 1994, ISBN 0-89603-268-X , pp. 329-334, doi : 10.1385 / 0-89603 -268-X: 329 .
5. ^ David M. Jameson: Gregorio Weber, 1916-1997: a fluorescent lifetime. In: Biophysical Journal. Volume 75, Number 1, July 1998, pp. 419-421, doi : 10.1016 / S0006-3495 (98) 77528-9 , PMID 9649401 , PMC 1299713 (free full text).
6. ↑ T. Kinoshita, F. Iinuma, A. Tsuji: 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. In: Chemical & Pharmaceutical Bulletin. 22, No. 10, 1974, pp. 2413-2420, PMID 4468087 .
7. ^ RE Boyle: The Reaction of Dimethyl Sulfoxide and 5-Dimethylaminonaphthalene-1-sulfonyl Chloride. In: The Journal of Organic Chemistry 31, No. 11, 1966, pp. 3880-3882, doi : 10.1021 / jo01349a529 .