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Bis(2-mercaptoethyl)sulfone (CAS 145626-87-5)

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Alternate Names:
BMS
Application:
Bis(2-mercaptoethyl)sulfone is a disulfide reducing agent replacement for DTT
CAS Number:
145626-87-5
Purity:
≥96%
Molecular Weight:
186.32
Molecular Formula:
C4H10O2S3
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Bis(2-mercaptoethyl)sulfone (BMS) is a symmetric bisthiol sulfone compound. Bis(2-mercaptoethyl)sulfone has been described as a useful compound for the reduction of disulfides in aqueous solutions. Also, Bis(2-mercaptoethyl)sulfone is a water-soluble reagent that is useful for the reduction of native disulfide bonds in proteins. It is considered to be a superior reducing agent to DTT. Bis(2-mercaptoethyl)sulfone has shown to reduce accessible disulfide bonds in immunoglobulin and trypsinogen under non-denaturing conditions 5 to 7 times faster than DTT at pH 7. The relatively less accessible disulfide bond in alpha-chymotrypsinogen A was reduced 2.3 times faster at with BMS than with DTT at pH 7.0.


Bis(2-mercaptoethyl)sulfone (CAS 145626-87-5) References

  1. Two critical cysteine residues implicated in disulfide bond formation and proper folding of Kir2.1.  |  Cho, HC., et al. 2000. Biochemistry. 39: 4649-57. PMID: 10769120
  2. First total synthesis of mycothiol and mycothiol disulfide.  |  Lee, S. and Rosazza, JP. 2004. Org Lett. 6: 365-8. PMID: 14748594
  3. Imaging dynamic redox changes in mammalian cells with green fluorescent protein indicators.  |  Dooley, CT., et al. 2004. J Biol Chem. 279: 22284-93. PMID: 14985369
  4. Determination of denaturated proteins and biotoxins by on-line size-exclusion chromatography-digestion-liquid chromatography-electrospray mass spectrometry.  |  Carol, J., et al. 2005. Anal Biochem. 346: 150-7. PMID: 16185643
  5. Mutations in Orai1 transmembrane segment 1 cause STIM1-independent activation of Orai1 channels at glycine 98 and channel closure at arginine 91.  |  Zhang, SL., et al. 2011. Proc Natl Acad Sci U S A. 108: 17838-43. PMID: 21987804
  6. Permeation, selectivity and gating in store-operated CRAC channels.  |  McNally, BA. and Prakriya, M. 2012. J Physiol. 590: 4179-91. PMID: 22586221
  7. Phosphines are ribonucleotide reductase reductants that act via C-terminal cysteines similar to thioredoxins and glutaredoxins.  |  Domkin, V. and Chabes, A. 2014. Sci Rep. 4: 5539. PMID: 24986213
  8. Communication between N terminus and loop2 tunes Orai activation.  |  Fahrner, M., et al. 2018. J Biol Chem. 293: 1271-1285. PMID: 29237733
  9. Stabilizing DNA nanostructures through reversible disulfide crosslinking.  |  Wolfrum, M., et al. 2019. Nanoscale. 11: 14921-14928. PMID: 31360975
  10. Breaking a Couple: Disulfide Reducing Agents.  |  Mthembu, SN., et al. 2020. Chembiochem. 21: 1947-1954. PMID: 32196882
  11. Synthesis of dithiols as reducing agents for disulfides in neutral aqueous solution and comparison of reduction potentials  |  Lamoureux, G. V., & Whitesides, G. M. 1993. The Journal Of Organic Chemistry. 58(3): 633-641.
  12. Selenol-catalyzed reduction of disulfide bonds in peptides and proteins  |  Singh, R. 1996. Techniques in Protein Chemistry. 7: 221-230.
  13. Recombinant Lactobacillus leichmannii ribonucleosidetriphosphate reductase as biocatalyst in the preparative synthesis of 2′-deoxyribonucleoside-5′-triphosphates  |  Brunella, A., & Ghisalba, O. 2000. Journal of Molecular Catalysis B: Enzymatic. 10(1-3): 215-222.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Bis(2-mercaptoethyl)sulfone, 1 g

sc-210935
1 g
$765.00

What is the solubility of this product?

Asked by: hawkeye11
The product is soluble in DMSO, Ethanol, H2O (1.8 mg/ml), or Methanol. May require warming (40-45°C) to achieve complete solubilization in H2O.
Answered by: Tech Service 4
Date published: 2016-12-17
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Rated 5 out of 5 by from Various publications cite the use of Bis(2Various publications cite the use of Bis(2-mercaptoethyl)sulfone as a reducing agent of disulfides in aqueous solutions. -SCBT Publication Review
Date published: 2015-03-27
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Bis(2-mercaptoethyl)sulfone is rated 5.0 out of 5 by 1.
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