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(±)-trans-1,2-Bis(2-mercaptoacetamido)cyclohexane (CAS 257641-01-3)

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Alternate Names:
Vectrase P; 2-sulfanyl-N-[2-[(2-sulfanylacetyl)amino]cyclohexyl]acetamide
Application:
(±)-trans-1,2-Bis(2-mercaptoacetamido)cyclohexane is a useful disulfide-containing protein refolding agent
CAS Number:
257641-01-3
Purity:
98%
Molecular Weight:
262.39
Molecular Formula:
C10H18N2O2S2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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(±)-trans-1,2-Bis(2-mercaptoacetamido)cyclohexane is a cyclohexane compound substituted with two mercaptoacetamido groups. (±)-trans-1,2-Bis(2-mercaptoacetamido)cyclohexane has been described to effectively accelerate oxidative protein folding through interaction with thiol-disulfide exchange reactions, and was demonstrated to be particularly effective in refolding disulfide-containing proteins.


(±)-trans-1,2-Bis(2-mercaptoacetamido)cyclohexane (CAS 257641-01-3) References

  1. A small-molecule catalyst of protein folding in vitro and in vivo.  |  Woycechowsky, KJ., et al. 1999. Chem Biol. 6: 871-9. PMID: 10631515
  2. Aromatic thiol pKa effects on the folding rate of a disulfide containing protein.  |  Gough, JD., et al. 2003. Biochemistry. 42: 11787-97. PMID: 14529290
  3. Investigation of protein refolding using a fractional factorial screen: a study of reagent effects and interactions.  |  Willis, MS., et al. 2005. Protein Sci. 14: 1818-26. PMID: 15937284
  4. Structural determinants of substrate access to the disulfide oxidase Erv2p.  |  Vala, A., et al. 2005. J Mol Biol. 354: 952-66. PMID: 16288914
  5. Non-redox-active small-molecules can accelerate oxidative protein folding by novel mechanisms.  |  Fink, M., et al. 2008. Biophys Chem. 132: 104-9. PMID: 18045767
  6. Small-molecule catalysts of oxidative protein folding.  |  Lees, WJ. 2008. Curr Opin Chem Biol. 12: 740-5. PMID: 18824127
  7. Small-molecule diselenides catalyze oxidative protein folding in vivo.  |  Beld, J., et al. 2010. ACS Chem Biol. 5: 177-82. PMID: 20052969
  8. Optimization of oxidative folding methods for cysteine-rich peptides: a study of conotoxins containing three disulfide bridges.  |  Steiner, AM. and Bulaj, G. 2011. J Pept Sci. 17: 1-7. PMID: 20814907
  9. Acyl cystamine: small-molecular foldase mimics accelerating oxidative refolding of disulfide-containing proteins.  |  Wang, GZ., et al. 2011. Biotechnol Prog. 27: 377-85. PMID: 21302368
  10. Efficacy of peptide nucleic acid and selected conjugates against specific cellular pathologies of amyotrophic lateral sclerosis.  |  Browne, EC., et al. 2016. Bioorg Med Chem. 24: 1520-7. PMID: 26935939
  11. The Redox Activity of Protein Disulfide Isomerase Inhibits ALS Phenotypes in Cellular and Zebrafish Models.  |  Parakh, S., et al. 2020. iScience. 23: 101097. PMID: 32446203
  12. Peptide disulfides CGC and RKCGC facilitate oxidative protein refolding  |  Guo-Zhen Wang, Xiaoyan Dong, Yan Sun. 2011. Biochemical Engineering Journal. Volume 55, Issue 3: 169-175.
  13. Peptide disulfide RKCGCFF facilitates oxidative protein refolding by mimicking protein disulfide isomerase  |  Hu Liu, Xiao-Yan Dong, Yan Sun. 2013. Biochemical Engineering Journal. 79: 29-32.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

(±)-trans-1,2-Bis(2-mercaptoacetamido)cyclohexane, 100 mg

sc-213078
100 mg
$372.00

What is the solubility of this product?

Asked by: hawkeye11
Thank you for your question. This chemical, +/-)-trans-1,2-Bis(2-mercaptoacetamido)cyclohexane: sc-213078, is soluble in >2 mg/mL in methanol.
Answered by: Technical Support
Date published: 2018-07-23
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Rated 5 out of 5 by from WinterWinter, J. et al. (PubMed 12167542) reported that (+/-)-trans-1,2-Bis(2-mercaptoacetamido)cyclohexane stimulated recombinant expression and in vitro folding of proinsulin. -SCBT Publication Review
Date published: 2015-03-20
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(±)-trans-1,2-Bis(2-mercaptoacetamido)cyclohexane is rated 5.0 out of 5 by 1.
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