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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
BGBB9121
BGBB6999
BGBB4919V
1435492
1435482

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G J Stephens et al.
Pflugers Archiv : European journal of physiology, 431(3), 435-442 (1996-01-01)
The effects of cysteine-modifying reagents on the gating of rat cloned Kv1.4 channels expressed in HEK-293 cells were examined using the whole-cell patch-clamp technique. Cells transfected with Kv1.4 expressed a rapidly inactivating K+ current with a mid-point of activation of
A Li et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 18(17), 6740-6747 (1998-08-26)
Functional modifications of neuronal P/Q-type voltage-dependent Ca2+ channels expressed in Xenopus oocytes by oxidation were examined electrophysiologically. Oxidation by external H2O2 enhanced the whole-oocyte currents through the Ca2+ channels composed of the alpha1A, alpha2/delta, and beta3 subunits at negative voltages
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
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
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
View All Related Papers

Global Trade Item Number

SKUGTIN
158194-10G4061832544670
158194-1G4061825970103

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