Thermo Scientific™ SMCC (succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate), 10 x 1 mg

Thermo Scientific™ SMCC (succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate), 10 x 1 mg

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.

Features

• 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.