Sulpho-SMCC (3-Sulpho-N-succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate sodium salt), Pierce™

Supplier: Thermo Fisher Scientific
Warning

Synonyms: Sodium 1-((4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexane-1-carbonyl)oxy)-2,5-dioxopyrrolidine-3-sulphonate, Sulphosuccinimidyl-trans-4-(N-maleimidomethyl)cyclohexane-1-carboxylate, Sulpho-SMCC Sodium Salt, SMCC, Water-Soluble, 4-(N-Maleimidomethyl)cyclohexane-1-carboxylic acid 3-sulpho-N-hydroxysuccinimide ester sodium salt, sulpho-SMCC, Sulfo-SMCC

22322 22122
PIER22322EA 367 GBP
PIER22322 PIER22122
Sulpho-SMCC (3-Sulpho-N-succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate sodium salt), Pierce™
Sulpho-SMCC (3-Sulpho-N-succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate sodium salt)

Thermo Scientific Pierce Sulfo-SMCC, No-Weigh Format is a water-soluble, amine-to-sulfhydryl crosslinker that contains NHS-ester and maleimide reactive groups at opposite ends of a medium-length cyclohexane spacer arm (8.3 angstroms).


  • Reactive groups: sulfo-NHS ester and maleimide
  • Reactive towards: amino and sulfhydryl groups
  • Water-soluble (compare to SMCC), so crosslinking can be done in physiologic solutions
  • High purity, crystalline reagent can be used to create high-purity maleimide-activated derivatives
  • Cyclohexane bridge confers added stability to the maleimide group making Sulfo-SMCC the ideal crosslinking agent for maleimide activation of proteins. Maleimide groups are stable for 64 hours in 0.1 M sodium phosphate buffer, pH 7 at 4°C.


Sulfosuccinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate (Sulfo-SMCC) is a non-cleavable and membrane impermeable crosslinker. It contains an amine-reactive N-hydroxysuccinimide (NHS ester) and a sulfhydryl-reactive maleimide group. NHS esters react with primary amines at pH 7-9 to form stable amide bonds. Maleimides react with sulfhydryl groups at pH 6.5-7.5 to form stable thioether bonds. The maleimide groups of Sulfo-SMCC and SMCC are unusually stable up to pH 7.5 because of the cyclohexane bridge in the spacer arm. Because it contains the hydrophilic sulfonyl moiety, Sulfo-SMCC is soluble up to ∼10 mM in water and many commonly used buffers, thus avoiding the use of organic solvents which may perturb protein structure.


Caution: For Research Use Only. Not for use in diagnostic procedures.

Formula: C₁₆H₁₈N₂O₉S
MW: 436,37 g/mol
Melting Pt: 179 °C
Storage Temperature: Freezer
MDL Number: MFCD00054978
CAS Number: 92921-24-9

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Specification Test Results

Product Line Pierce™
Labeling Method Chemical Labeling
Crosslinker Type Heterobifunctional
Reactive Moiety Maleimide, Sulfo-NHS Ester
Spacer Short
Form Powder
Quantity 50 mg/1 g
Type Crosslinker
Solubility Water

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