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.
- Convert sulfhydryl groups to carboxyl groups for conjugation to amines via carbodiimide (EDC)
- Prepare maleimide-activated proteins using EDC to modify primary amines
- Maleimides react with –SH groups at pH 6.5-7.5, forming stable thioether linkages
Structure and properties of EMCA:
- Functional groups: maleimide (sulfhydryl-reactive) and carboxyl
- 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
Overview of crosslinking and protein modification