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Safety Information

253367

Sigma-Aldrich

4-(2-Iodoacetamido)-TEMPO

free radical

Synonym(s):

4-(2-Iodoacetamido)-2,2,6,6-tetramethyl-1-piperidinyloxy, free radical, 4-(2-Iodoacetamido)-2,2,6,6-tetramethylpiperidine 1-oxyl

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About This Item

Empirical Formula (Hill Notation):
C11H20IN2O2
CAS Number:
25713-24-0
Molecular Weight:
339.19
MDL number:
MFCD00010171
UNSPSC Code:
12352101
PubChem Substance ID:
24855308
NACRES:
NA.22

form

solid

mp

114-117 °C (lit.)

functional group

amide
iodo

storage temp.

2-8°C

SMILES string

CC1(C)CC(CC(C)(C)N1[O])NC(=O)CI

InChI

1S/C11H20IN2O2/c1-10(2)5-8(13-9(15)7-12)6-11(3,4)14(10)16/h8H,5-7H2,1-4H3,(H,13,15)

InChI key

UCTVRHAKQRFPEZ-UHFFFAOYSA-N

Application

Methionine-specific spin label.
Spin label used to investigate the binding site of phosphoenolpyruvate caboxykinase and GTP, and to evaluate the alkylation of SH1 and SH2 of myosin.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
12409MS
07124CZ

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P G Fajer
Biophysical journal, 66(6), 2039-2050 (1994-06-01)
The determination of the iodoacetamide spin label orientation in myosin heads (Fajer, 1994) allows us for the first time to determine directly protein orientation from EPR spectra. Computational simulations have been used to determine the sensitivity of EPR to both
J E Mahaney et al.
Biochemistry, 34(14), 4864-4879 (1995-04-11)
We have used time-resolved electron paramagnetic resonance (EPR) and quenched-flow kinetics in order to investigate the dynamics of Ca-ATPase conformational changes involved in Ca2+ pumping in sarcoplasmic reticulum (SR) membranes at 2 degrees C. The Ca-ATPase was selectively labeled with
V P Timofeev et al.
Biophysics of structure and mechanism, 7(1), 41-49 (1980-01-01)
The rotational correlation time of two homologous cytoplasmic aspartate aminotransferase molecules isolated from pig and chicken hearts was obtained by spin-labeling technique. The maleimide and iodoacetamide spin-labels modifying external SH-groups of a protein were used. In the interpretation of ESR
G Pitari et al.
Journal of protein chemistry, 18(7), 785-789 (2000-02-26)
Conformational changes at the active site of pantetheine hydrolase (EC3.5.1.-) during guanidine hydrochloride (GndHCl) denaturation were investigated by UV and circular dichroism spectroscopy and by electron spin resonance spectroscopy, following the spectral behaviour of the nitroxide radicals (N-(1-oxyl-2,2,5,5,-tetramethyl-3-pyrrolidinyl) iodacetamide) covalently
V A Barnett et al.
Biochemistry, 26(1), 314-323 (1987-01-13)
We have measured the conventional electron paramagnetic resonance (EPR) spectrum of spin-labeled myosin filaments as a function of the nucleotide occupancy of the active site of the enzyme. The probe used was 4-(2-iodoacetamido)-2,2,6,6-tetramethylpiperidine-1-oxyl (IASL), which reacts specifically with sulfhydryl 1
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