Sulfo SMCC (Sulfosuccinimidyl-4-(N-maleimidomethyl)cyclohexane- 1-carboxylate)

General description

Sulfosuccinimidyl-4-(N-maleimidomethyl) cyclohexane-1-carboxylate (Sulfo-SMCC) is a water-soluble, non-cleavable and membrane impermeable crosslinker containing 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. Due to the presence of a 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 the protein structure.

Applications:

• enzyme labeling of antibodies – both enzyme 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