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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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MXP 1,445.00
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MXP 6,896.00

MXP 1,445.00

Estimated to ship onApril 17, 2025

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1 G
MXP 1,445.00
10 G
MXP 6,896.00

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

MXP 1,445.00

Estimated to ship onApril 17, 2025

Request a Bulk Order

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.[1]

Application

2,2′-Dithiobis(5-nitropyridine) was employed:
  • as cysteine-activating reagent to study the NMR of G protein-coupled receptors[2]
  • in the deprotection assays for protected selenocysteine-containing peptides[3]
  • for deprotecting p-methoxybenzyl groups and acetamidomethyl groups from the side-chains of cysteine and selenocysteine[1]
  • to remove the p-methoxybenzyl protecting group from cysteine and selenocysteine side-chains[1]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000249748
0000297960
0000265623
0000265624
0000175279

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K Yamaoka et al.
Pflugers Archiv : European journal of physiology, 440(2), 207-215 (2000-07-18)
The effects of sulfhydryl (SH) reagents on the L-type Ca current (ICa) were studied in frog ventricular myocytes using the whole-cell patch-clamp method. Methanethiosulfonate ethylammonium (MTSEA+) was found to enter the cell through the membrane and cause a remarkable increase
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
Effects of oxidants on membrane potential, K+ and Ca2+ currents of mouse pancreatic B-cells.
P Krippeit-Drews et al.
Advances in experimental medicine and biology, 426, 355-359 (1997-01-01)
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.
Uncoupling and energy transfer inhibition of photophosphorylation by sulfhydryl reagents.
J V Moroney et al.
The Journal of biological chemistry, 255(14), 6670-6674 (1980-07-25)
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