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Sigma-Aldrich

N-(Iodoacetaminoethyl)-1-naphthylamine-5-sulfonic acid

suitable for fluorescence, ≥95% (HPLC)

Synonym(s):

1,5-I-AEDANS, 5-[2-(Iodoacetamido)ethylamino]naphthalene-1-sulfonic acid, N-Iodoacetyl-N′-(5-sulfo-1-naphthyl)ethylenediamine, Hudson-Weber-Reagent

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About This Item

Linear Formula:
ICH2CONHCH2CH2NHC10H6SO3H
CAS Number:
36930-63-9
Molecular Weight:
434.25
Beilstein:
3004454
EC Number:
253-277-7
MDL number:
MFCD00003993
UNSPSC Code:
12352200
eCl@ss:
32035301
PubChem Substance ID:
329758333

Assay

≥95% (HPLC)

fluorescence

λex 336 nm; λem 490 nm (pH 8.0)
λex 337 nm; λem 498 nm (after derivatization with 2-mercaptoethanol)

suitability

suitable for fluorescence

storage temp.

2-8°C

SMILES string

OS(=O)(=O)c1cccc2c(NCCNC(=O)CI)cccc12

InChI

1S/C14H15IN2O4S/c15-9-14(18)17-8-7-16-12-5-1-4-11-10(12)3-2-6-13(11)22(19,20)21/h1-6,16H,7-9H2,(H,17,18)(H,19,20,21)

InChI key

ZMERMCRYYFRELX-UHFFFAOYSA-N

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Application

N-(Iodoacetaminoethyl)-1-naphthylamine-5-sulfonic acid (1,5-I-AEDANS) is a fluorescence probe used to label protein sulfhydryls to study conformational changes, fluorescence anisotropy and protein:protein interactions.

Other Notes

Fluorescent sulfhydryl reagent

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Jason R Waggoner et al.
Biochemistry, 46(7), 1999-2009 (2007-01-31)
We have used steady-state fluorescence spectroscopy in combination with enzyme kinetic assays to test the hypothesis that phospholamban (PLB) stabilizes the Ca-ATPase in the E2 intermediate state. The cardiac muscle Ca-ATPase (SERCA2a) isoform was expressed either alone or coexpressed with
Samrat Mukhopadhyay et al.
Journal of molecular biology, 358(4), 935-942 (2006-03-21)
The small protein barstar aggregates at low pH to form soluble oligomers, which can be transformed into fibrillar aggregates at an elevated temperature. To characterize structurally, with residue-specific resolution, the process of amyloid formation of barstar, as well as to
Torsten Heidenreich et al.
The Journal of biological chemistry, 280(6), 4213-4218 (2004-11-25)
The molybdenum cofactor sulfurase ABA3 from Arabidopsis thaliana specifically regulates the activity of the molybdenum enzymes aldehyde oxidase and xanthine dehydrogenase by converting their molybdenum cofactor from the desulfo-form into the sulfo-form. ABA3 is a two-domain protein with an NH2-terminal
Adrienne Clements et al.
Analytical chemistry, 77(14), 4495-4502 (2005-07-15)
This study demonstrates that 1,5-I-AEDANS (5-({2-[(iodoacetyl)amino]ethyl}amino)naphthalene-1-sulfonic acid) can be used as a versatile fluorescence-based peptide quantification tool and provides readily interpretable tandem mass spectra for de novo peptide sequencing. Two AEDANS-cysteinyl-peptide fractionation strategies were evaluated. One AEDANS-cysteinyl-peptide fractionation strategy employs
Joseph J Kehoe et al.
Journal of agricultural and food chemistry, 55(17), 7107-7113 (2007-07-26)
This paper takes a new approach to determining which sulfhydryl groups are exposed during the heat denaturation of bovine beta-lactoglobulin A. The sulfhydryl groups exposed after heating were blocked with 5-((((2-iodoacetyl)amino)ethyl)amino)naphthalene-1-sulfonic acid (IAEDANS). The results show that IAEDANS is a
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