09278
4-[4-(Dimethylamino)phenylazo]benzoic acid N-succinimidyl ester
≥98.0% (HPLC)
Synonym(s):
4-(Dimethylamino)azobenzene-4′-carboxylic acid N-succinimidyl ester, DABCYL-N-succinimidyl ester
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About This Item
Empirical Formula (Hill Notation):
C19H18N4O4
CAS Number:
Molecular Weight:
366.37
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.32
MDL number:
InChI
1S/C19H18N4O4/c1-22(2)16-9-7-15(8-10-16)21-20-14-5-3-13(4-6-14)19(26)27-23-17(24)11-12-18(23)25/h3-10H,11-12H2,1-2H3/b21-20+
InChI key
IBOVDNBDQHYNJI-QZQOTICOSA-N
assay
≥98.0% (HPLC)
form
powder
solubility
DMF: soluble, DMSO: soluble
fluorescence
λex 428 nm; λem 453 nm
storage temp.
−20°C
Quality Level
Application
A useful reagent (similar to MANCYL-SE) for labeling proteins or peptides through their amino-groups by forming stable peptide bonds. The succinimidyl ester is reactive with terminal amines or lysines of peptides and other nucleophiles for fluorescent studies of proteins. Its fluorescent properties (has a characteristic broad and intense visible absorption but has no fluorescence) make it an ideal long wavelength quencher and it has been utilized as an acceptor chromophore in FRET studies.
Analysis Note
Absorption spectra shows a maximum at 453 nm (in methanol). After reaction with butylamine: max. absorption at 428 nm (Lit.)
Other Notes
N-terminal modification of peptides in automated synthesis
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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L L Maggiora et al.
Journal of medicinal chemistry, 35(21), 3727-3730 (1992-10-16)
A general scheme for obtaining a fluorescent donor/acceptor peptide substrate via solid-phase synthesis methodology is presented. The key feature of this method is the design of a glutamic acid derivative that has been modified on the carboxyl side chain with
C García-Echeverría et al.
FEBS letters, 297(1-2), 100-102 (1992-02-03)
A series of new substrates for determining the catalytic activity of cysteine proteinases is described. The rate of hydrolysis by papain was monitored by a fluorescence continuous assay based on internal resonance energy transfer using 5-[(2-aminoethyl)amino]naphtalene-1-sulfonic acid (EDANS) and 4-(4-dimethylaminophenylazo)benzoic
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