5-Maleimido-2-hydraziniumpyridine hydrochloride
Cat No.: BP-502177
4.5 
5-Maleimido-2-hydraziniumpyridine hydrochloride is a heteroaromatic linker reagent that combines a pyridine scaffold with a maleimide electrophile and a hydrazinium functionality, enabling orthogonal, covalent conjugation strategies commonly used in PROTAC and targeted protein degradation workflows. The maleimide group reacts selectively with thiol-containing residues (for example, cysteine or engineered thiol tags) via a Michael-type addition, providing a stable thioether linkage that can tether a ligand or protein-binding module to a degradation construct. In parallel, the hydrazinium component supports controlled handling and reactivity tuning during synthesis and assembly, helping researchers build modular architectures where the linker preserves the binding properties of the recruited ligand. This reagent is valuable for preparing well-defined PROTAC intermediates, enabling precise attachment of functional domains and facilitating comparative studies of linker length, attachment chemistry, and resulting degradation potency in cellular assays.
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* For research and manufacturing use only. Not for human or clinical use.
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5-Maleimido-2-hydraziniumpyridine hydrochloride is a bifunctional PROTAC linker building block designed to connect a maleimide-reactive handle with a hydrazinium-bearing pyridine motif, enabling controlled assembly of targeted protein degraders. Its electrophilic maleimide functionality supports robust conjugation to suitable nucleophiles, while the pyridinium/hydrazinium component provides a chemically addressable attachment site for integrating ligands. The combination of orthogonal reactivity and practical synthetic compatibility makes it well suited for constructing PROTAC architectures; detailed structural and reactivity considerations are provided below.
Structure: The molecule contains a maleimide ring bearing an electrophilic double bond, alongside a pyridine core substituted with a hydrazinium functionality. As a hydrochloride salt, it features protonated ionic character, supporting water-compatible handling. Key features include conjugated unsaturation in the maleimide and heteroatom-rich linkages.
Reactivity: PROTAC assembly using this linker typically relies on nucleophilic addition to the maleimide under mild conditions, commonly with thiol-containing partners to form stable thioether adducts. The maleimide reacts via a Michael-type addition followed by adduct formation, and reaction performance depends on maintaining an appropriate pH window to preserve nucleophile availability while avoiding maleimide hydrolysis. Solvents such as aqueous buffers with compatible organic cosolvents are commonly used, and no special catalysts are generally required for the conjugation step.
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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