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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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Alayne L Schroll et al.
Journal of peptide science : an official publication of the European Peptide Society, 18(1), 1-9 (2011-11-16)
Of all the commercially available amino acid derivatives for solid phase peptide synthesis, none has a greater abundance of side-chain protection diversity than cysteine. The high reactivity of the cysteine thiol necessitates its attenuation during peptide construction. Moreover, the propensity
P Sharma et al.
Analytical biochemistry, 189(2), 173-177 (1990-09-01)
A sensitive and simple method is described for the quantitative determination of free sulfhydryl (-SH) groups on polymer supports. The method includes the reaction of 4,4'-dimethoxytrityloxy-S-(2-thio-5-nitropyridyl)-2-mercapto ethane (DTNPME) with polymer-supported sulfhydryl groups. After removal of excess reagent through washing, a
Leah S Cohen et al.
Biopolymers, 102(1), 16-29 (2013-07-31)
Structural analysis by NMR of G protein-coupled receptors (GPCRs) has proven to be extremely challenging. To reduce the number of peaks in the NMR spectra by segmentally labeling a GPCR, we have developed a Guided Reconstitution method that includes the
M K Park et al.
Experimental physiology, 80(5), 835-842 (1995-09-01)
Ca(2+)-activated K+ currents (IK(Ca)) and voltage-dependent Ca(2+)-insensitive K+ currents (IK(V)) were recorded using the patch clamp technique to study the pulmonary (PASMC) and ear arterial smooth muscle cells (EASMC) of the rabbit and the possible regulatory mechanisms related to hypoxia.
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
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