Dabsyl chloride

Structural formula
General
Surname	Dabsyl chloride
other names	Dabs-Cl; 4-methylaminoazobenzene-4'-sulfonyl chloride ( IUPAC ) ;
Molecular formula	C 14 H 14 ClN 3 O 2 S
Brief description	dark red, crystalline
External identifiers / databases
EC number	260-235-1
ECHA InfoCard	100.054.742
PubChem	91660
ChemSpider	82763
Wikidata	Q29354953
properties
Molar mass	323.79 g mol −1
Physical state	firmly
Melting point	185 ° 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 .

Dabsyl chloride (from diaminobenzenesulfonyl chloride ) is an organic benzosulfonyl chloride that serves as a detection reagent .

Dabsyl chloride is used in protein analysis for precolumn derivatization of primary and secondary amines in HPLC . The amino group is derivatized with the reagent:

The derivative then shows absorption at 436 nm and offers a sensitivity of 1 pmol. The dabsyl amino acids formed are stable for several weeks.

In nucleic acid analysis, dabsyl chloride can be used as a quencher for fluorescence markers, for example for the detection of certain RNA sequences. An RNA probe is equipped with the quencher (dabsyl chloride) directly at the 5 'end and the fluorophore about two nucleotides in front of it. A second probe is equipped with a phosphorothioate group on the ribonucleotide at the 3 'end. If both probes with the sequence sought form base pairings , the sulfur can remove the dabsyl chloride from the phosphorothioate group by means of an S _N 2 substitution at C5 and the fluorescent marker becomes detectable.

Individual evidence

↑ ^a ^b ^c ^d data sheet Dabsyl chloride at Sigma-Aldrich , accessed on April 12, 2017 ( PDF ).
^ Friedrich Lottspeich, Joachim W. Engels (Ed.): Bioanalytik . 3. Edition. Springer Spectrum, Berlin / Heidelberg 2012, ISBN 978-3-8274-2942-1 , p. 341 f .
^ Daniel Krois: Organic-chemical methods . Springer Berlin Heidelberg, Berlin / Heidelberg 2017, ISBN 978-3-662-53013-9 , pp. 170-172 .

[SIGMA-1] ta sheet Dabsyl chloride at Sigma-Aldrich , accessed on April 12, 2017 ( PDF ).

[lottspeich-2] Friedrich Lottspeich, Joachim W. Engels (Ed.): Bioanalytik . 3. Edition. Springer Spectrum, Berlin / Heidelberg 2012, ISBN 978-3-8274-2942-1 , p. 341 f .

[krois-3] Daniel Krois: Organic-chemical methods . Springer Berlin Heidelberg, Berlin / Heidelberg 2017, ISBN 978-3-662-53013-9 , pp. 170-172 .