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158194

Sigma-Aldrich

2,2′-Dithiobis(5-nitropyridine)

96%

Synonym(s):

Bis(5-nitro-2-pyridyl) disulfide, DTNP

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About This Item

Empirical Formula (Hill Notation):
C10H6N4O4S2
CAS Number:
2127-10-8
Molecular Weight:
310.31
Beilstein/REAXYS Number:
305413
EC Number:
218-344-7
MDL number:
MFCD00006453
UNSPSC Code:
12352100
PubChem Substance ID:
24849723
NACRES:
NA.22

assay

96%

form

solid

mp

155-157 °C (lit.)

functional group

disulfide
nitro

SMILES string

[O-][N+](=O)c1ccc(SSc2ccc(cn2)[N+]([O-])=O)nc1

InChI

1S/C10H6N4O4S2/c15-13(16)7-1-3-9(11-5-7)19-20-10-4-2-8(6-12-10)14(17)18/h1-6H

InChI key

ROUFCTKIILEETD-UHFFFAOYSA-N

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General description

2,2′-Dithiobis(5-nitropyridine) is an aromatic disulphide.

Application

2,2′-Dithiobis(5-nitropyridine) was employed:
  • as cysteine-activating reagent to study the NMR of G protein-coupled receptors
  • in the deprotection assays for protected selenocysteine-containing peptides
  • for deprotecting p-methoxybenzyl groups and acetamidomethyl groups from the side-chains of cysteine and selenocysteine
  • to remove the p-methoxybenzyl protecting group from cysteine and selenocysteine side-chains

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000249748
0000297960
0000265623
0000265624
0000175279

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Chi-Pan Hsieh
Biochemical and biophysical research communications, 370(3), 445-449 (2008-04-01)
Redox modulation of fast inactivation has been described in certain cloned A-type voltage-gated K(+) (Kv) channels in expressing systems, but the effects remain to be demonstrated in native neurons. In this study, we examined the effects of cysteine-specific redox agents
P Krippeit-Drews et al.
Biochemical and biophysical research communications, 200(2), 860-866 (1994-04-29)
The whole-cell patch-clamp technique has been applied to elucidate the effects of H2O2 and the SH-group reagent 2,2'-dithio-bis(5-nitropyridine) (DTBNP) on Ca2+ currents of mouse pancreatic B-cells. We also tested the effect of DTBNP on the whole-cell K+ ATP current. DTBNP
M S Islam et al.
FEBS letters, 319(1-2), 128-132 (1993-03-15)
Effects of sulfhydryl modification on the ATP regulated K+ channel (KATP channel) in the pancreatic beta-cell were studied, using the patch clamp technique. Application of the sulfhydryl oxidizing agents thimerosal and 2,2'-dithio-bis(5-nitropyridine) (DTBNP), in micromolar concentrations, caused complete inhibition of
M K Park et al.
Pflugers Archiv : European journal of physiology, 434(6), 764-771 (1997-11-05)
It has been suggested that hypoxic pulmonary vasoconstriction (HPV) results from the depolarization that is induced by the suppression of K+ current in pulmonary arterial smooth muscle cells (PASMC). We tested the hypothesis that the effect of the cellular redox
Alayne L Schroll et al.
Journal of peptide science : an official publication of the European Peptide Society, 18(3), 155-162 (2012-01-18)
In contrast to the large number of sidechain protecting groups available for cysteine derivatives in solid phase peptide synthesis, there is a striking paucity of analogous selenocysteine Se-protecting groups in the literature. However, the growing interest in selenocysteine-containing peptides and
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