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Sulfo-SMCC
A water-soluble amine-to-sulfhydryl crosslinker with a medium-length cyclohexane spacer arm (8.3 angstroms).
Thermo Scientific Pierce Sulfo-SMCC is a very popular, 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).
Sulfosuccinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate (Sulfo-SMCC) is a water-soluble, 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.
Sulfo-SMCC Highlights
Amine reactive Sulfo-NHS ester crosslinks rapidly with primary amine-containing molecule
Sulfhydryl-reactive maleimide reacts with cysteine residues to yield specific conjugates
Sulfo-SMCC is water soluble, so crosslinking can be done in physiologic solutions
High purity, crystalline Sulfo-SMCC 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.
Applications for Sulfo-SMCC
Ideal crosslinker for enzyme labeling of antibodies, both enzyme activity and antibody specificity can be preserved
Create specific bioconjugates via one- or two-step crosslinking reactions
Create sulfhydryl-reactive, maleimide-activated carrier proteins for coupling haptens |