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2,2′-Dithiobis(5-nitropyridine) (CAS 2127-10-8)

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Alternate Names:
Bis(5-nitro-2-pyridyl) disulfide; DTNP
Application:
2,2′-Dithiobis(5-nitropyridine) is a cysteine-activating reagent and for deprotecting and removing p-methoxybenzyl groups and acetamidomethyl groups
CAS Number:
2127-10-8
Purity:
≥96%
Molecular Weight:
310.31
Molecular Formula:
C10H6N4O4S2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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2,2′-Dithiobis(5-nitropyridine) is a chemical compound used primarily in the field of material science and photochemistry for its unique electron-accepting and photochemical properties. Its ability to form charge-transfer complexes makes it a candidate for studying electron transfer mechanisms. The nitro groups attached to the pyridine rings add to its electron-withdrawing strength, which is essential for research into the development of novel photovoltaic materials. Additionally, the disulfide bridge in the molecule can undergo cleavage and reformation, a feature that is exploited in research focusing on self-healing materials and reversible cross-linking in polymer networks. Its role in the formation of conductive polymers is also of interest, as these materials have applications in creating new types of electronic devices. Moreover, the compound′s ability to absorb light and undergo subsequent chemical transformations makes it a useful chromophore in the study of light-induced reactions and in the design of molecular electronics.


2,2′-Dithiobis(5-nitropyridine) (CAS 2127-10-8) References

  1. Studies on deprotection of cysteine and selenocysteine side-chain protecting groups.  |  Harris, KM., et al. 2007. J Pept Sci. 13: 81-93. PMID: 17031870
  2. Redox modulation of A-type K+ currents in pain-sensing dorsal root ganglion neurons.  |  Hsieh, CP. 2008. Biochem Biophys Res Commun. 370: 445-9. PMID: 18375201
  3. 2,2'-Dithiobis(5-nitropyridine) (DTNP) as an effective and gentle deprotectant for common cysteine protecting groups.  |  Schroll, AL., et al. 2012. J Pept Sci. 18: 1-9. PMID: 22083608
  4. The use of 2,2'-dithiobis(5-nitropyridine) (DTNP) for deprotection and diselenide formation in protected selenocysteine-containing peptides.  |  Schroll, AL., et al. 2012. J Pept Sci. 18: 155-62. PMID: 22249911
  5. Removal of the 5-nitro-2-pyridine-sulfenyl protecting group from selenocysteine and cysteine by ascorbolysis.  |  Ste Marie, EJ., et al. 2016. J Pept Sci. 22: 571-6. PMID: 27480992
  6. High-Yield Synthesis of Human Insulin-Like Peptide 5 Employing a Nonconventional Strategy.  |  Zaykov, AN., et al. 2018. Org Lett. 20: 3695-3699. PMID: 29874090
  7. Establishing a method of HPLC involving precolumn derivatization by 2,2'-dithiobis (5-nitropyridine) to determine the sulfites in shrimps in comparison with ion chromatography.  |  Yang, K., et al. 2019. Food Sci Nutr. 7: 2151-2158. PMID: 31289663
  8. Facile removal of 4-methoxybenzyl protecting group from selenocysteine.  |  Jenny, KA., et al. 2019. J Pept Sci. 25: e3209. PMID: 31410953
  9. Novel Cu(I)-5-nitropyridine-2-thiol Cluster with NIR Emission: Structural and Photophysical Characterization.  |  Hassanein, K., et al. 2022. J Phys Chem C Nanomater Interfaces. 126: 10190-10198. PMID: 35774291
  10. Determining simple sulfhydryl compounds (low molecular weight) and their contents in biological samples by using 2,2'-dithiobis-(5-nitropyridine).  |  Swatditat, A. and Tsen, CC. 1972. Anal Biochem. 45: 349-56. PMID: 5060597
  11. The use of 2,2'-dithiobis-(5-nitropyridine) as a selective reagent for the detection of thiols.  |  Grassetti, DR. and Murray, JF. 1969. J Chromatogr. 41: 121-3. PMID: 5780855
  12. Effects of SH-group reagents on Ca2+ and K+ channel currents of pancreatic B-cells.  |  Krippeit-Drews, P., et al. 1994. Biochem Biophys Res Commun. 200: 860-6. PMID: 8179620
  13. Sulfhydryl oxidation induces rapid and reversible closure of the ATP-regulated K+ channel in the pancreatic beta-cell.  |  Islam, MS., et al. 1993. FEBS Lett. 319: 128-32. PMID: 8454044
  14. Reduced dihydroxyacetone sensitivity and normal sensitivity to glyceraldehyde and oxidizing agent of ATP-sensitive K+ channels of pancreatic beta cells in NIDDM rats.  |  Song, DK., et al. 1997. J Korean Med Sci. 12: 286-92. PMID: 9288626
  15. Modulation of voltage-dependent K+ channel by redox potential in pulmonary and ear arterial smooth muscle cells of the rabbit.  |  Park, MK., et al. 1997. Pflugers Arch. 434: 764-71. PMID: 9306010

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2,2′-Dithiobis(5-nitropyridine), 1 g

sc-251822
1 g
$84.00