NHSestermaleimide
NHSestermaleimide is a class of heterobifunctional crosslinkers that incorporate an N-hydroxysuccinimide (NHS) ester on one end and a maleimide group on the other. This arrangement enables sequential conjugation: the NHS ester reacts with primary amines, such as lysine residues or N-terminal amines on proteins, forming stable amide bonds; the exposed maleimide group then reacts with thiols, typically cysteine residues, via a Michael-type addition to form a stable thioether linkage. The two reactive ends allow selective linking of amine-containing molecules to thiol-containing partners under mild, aqueous conditions.
Commercial derivatives of NHSestermaleimide often feature a chemical spacer between the NHS and maleimide groups. Well-known
Handling and storage require consideration of NHS ester hydrolysis in water, which reduces reactivity. Reagents are
See also: NHS ester chemistry, maleimide chemistry, heterobifunctional crosslinkers, SMCC.