SMCC (N-Succinimidyl 4-(N-Maleimidomethyl)cyclohexanecarboxylate), Pierce™
Supplier: Thermo Fisher ScientificTotal Ratings: 0
Avg. Ratings: 0.0 out of 5
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Warning
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Synonyms:
4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-succinimidyl ester
, N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate
, 4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester
, SMCC
, Succinimidyl-trans-4-(N-maleimidylmethyl)cyclohexane-1-carboxylate
, 2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate
Thermo Scientific Pierce SMCC is a hetero-bifunctional crosslinker 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, NHS ester hydrolytic degradation 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 lose its reaction specificity for sulfhydryls at pH values > 7.5. For these reasons, conjugations with these crosslinkers are usually performed at pH 7.2–7.5, with the NHS ester (amine-targeted) reacted before or simultaneous with the maleimide (sulfhydryl-targeted) reaction.
- Reactive groups: NHS ester and maleimide
- Reactive toward: amino and sulfhydryl groups
- Non-cleavable
- Water-insoluble (dissolve first in DMF or DMSO); compare to Sulfo-SMCC
- High purity, crystalline reagent can be used to create high-purity maleimide-activated derivatives
- Cyclohexane bridge confers added stability to the maleimide group making SMCC an 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.
Succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate (SMCC) is a non-cleavable and membrane permeable 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 SMCC and Sulfo-SMCC and are unusually stable up to pH 7.5 because of the cyclohexane bridge in the spacer arm.
Thermo Scientific provides also SMCC No-Weigh format article, specialty reagents in a pre-aliquoted format. The pre-weighed packaging prevents the loss of reagent reactivity and contamination over time by eliminating the repetitive opening and closing of the vial. The format enables use of a fresh vial of reagent each time, eliminating the hassle of weighing small amounts of reagents and reducing concerns over reagent stability.
Caution: For Research Use Only. Not for use in diagnostic procedures.
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Formula:
C₁₆H₁₈N₂O₆ MW: 334.33 g/mol Melting Pt: 179 °C Storage Temperature: Refrigerator |
MDL Number:
MFCD00009634 CAS Number: 64987-85-5 |
Specification Test Results
| Product Line | Pierce™ |
| Labeling Method | Chemical Labeling |
| Crosslinker Type | Heterobifunctional |
| Reactive Moiety | Maleimide, NHS Ester |
| Spacer | Short |
| Form | Powder |
| Quantity | 50 mg |
| Type | Crosslinker |
| Solubility | DMF, DMSO |
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