Sulpho-SMCC (3-Sulpho-N-succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate sodium salt), Pierce™
Supplier: Thermo Fisher Scientific
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Warning
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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
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 |
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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