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Sulfo-EMCS crosslinker

Cat. # Quantity Price Lead time Buy this product
PCL036_0050 50 mg Enquire in stock
PCL036_0100 100 mg Enquire in stock
  • IUPAC Name: N-ε-maleimidocaproyl-oxysulfosuccinimide ester
  • Synonyms: Sulfo-EMCS, (N-(ε-maleimidocaproyloxy) sulfosuccinimide ester)
  • CAS: 103848-61-9 (of acid)
  • Smiles: O=C(CC1S(=O)([O-])=O)N(OC(CCCCCN2C(C=CC2=O)=O)=O)C1=O.[Na+]
  • Chemical formula: C14H16N2NaO9S
  • Molecular weight: 410.33
  • Purity: 95%+

EMCS and its water-soluble analog Sulfo-EMCS are heterobifunctional cross-linkers that contain N-hydroxysuccinimide (NHS) ester and maleimide groups that allow covalent conjugation of amine- and sulfhydryl-containing molecules. NHS esters react with primary amines at pH 7-9 to form amide bonds, while maleimides react with sulfhydryl groups at pH 6.5-7.5 to form stable thioether bonds. In aqueous solutions, hydrolytic degradation of the NHS ester is a competing reaction whose rate increases with pH. The maleimide group is more stable than the NHS-ester group but will slowly hydrolyze and also lose its reaction specificity for sulfhydryls at pH values > 7.5. For these reasons, conjugation experiments involving these cross-linkers are usually performed at pH 7.2-7.5, with the NHS-ester (amine-targeted) reaction being accomplished before or simultaneous with the maleimide (sulfhydryl-targeted) reaction.

Features and Benefits

     

  • Reactive groups: sulfo-NHS ester and maleimide
  • Reactive towards: amino and sulfhydryl groups
  • Sulfo-NHS ester end couples with primary amines at pH 7-9 to form stable amide bonds
  • Maleimide reacts with -SH groups at pH 6.5-7.5, forming stable thioether linkages
  • Non-cleavable
  • Water-soluble (compare to EMCS)
  • Aliphatic spacer offers low potential for eliciting an immune response
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