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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:
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.)

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
J Schneider et al.
Journal of virology, 33(2), 597-605 (1980-02-01)
Roughly 10% of surface glycoproteins in the envelope of mature Friend murine leukemia virus are coupled to membrane polypeptides by disulfide bridges. The remaining 90% of these glycoproteins are associated noncovalently. However, they could also be linked to membrane polypeptides
Katharine M Harris et al.
Journal of peptide science : an official publication of the European Peptide Society, 13(2), 81-93 (2006-10-13)
We present here a simple method for deprotecting p-methoxybenzyl groups and acetamidomethyl groups from the side-chains of cysteine and selenocysteine. This method uses the highly elecrophilic, aromatic disulfides 2,2'-dithiobis(5-nitropyridine) (DTNP) and 2,2'-dithiodipyridine (DTP) dissolved in TFA to effect removal of
Yu Qi et al.
Nature communications, 11(1), 1262-1262 (2020-03-11)
Binding of biomolecules to crystal surfaces is critical for effective biological applications of crystalline nanomaterials. Here, we present the modulation of exposed crystal facets as a feasible approach to enhance specific nanocrystal-biomolecule associations for improving cellular targeting and nanomaterial uptake.
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