Thermo Scientific Pierce EMCA is a carboxylic acid compound with a terminal maleimide group that can modify proteins and other molecules by EDC-mediated and sulfhydryl-targeted conjugation.
EMCA (N-epsilon-maleimidocaproic acid) is a heterobifunctional crosslinker that reacts with sulfhydryl groups to present a terminal carboxyl group. Additionally, the carboxyl can be coupled to amine-containing molecules using the water-soluble carbodiimide EDC. The EDC reaction results in an intermediate ester, which can react with primary amines to form amide bonds. Thus, amine-containing molecules can be modified to contain sulfhydryl-reactive maleimides.
- Sulfhydryl- and amine-reactive via water-soluble carbodiimide (EDC) coupling
- Prepare maleimide-activated proteins using EDC
- Maleimides react with –SH groups at pH 6.5-7.5, forming stable thioether linkages
- Modify protein sulfhydryl groups to carboxyl groups
- Reactive groups: maleimide and carboxyl
- Reactive toward: sulfhydryl and amino groups (when used with EDC)
- Chemical name: N-epsilon-maleimidocaproic acid
- Synonym: 6-maleimidohexanoic acid
- Chemical formula: C10H13NO4
- Molecular weight: 211.21
- Form: White to off-white solid, free of foreign material
- Griffith, D.G., et al. (1981). N-Polymethylene-carboxy-maleimides. A new class of probes for membrane sulfhydryl groups. FEBS Lett 134:261-3
EDC – A carbodiimide crosslinker for zero-length, carboxyl-to-amine conjugation