11-Maleimidoundecanoic acid is a bifunctional linker featuring a terminal maleimide group for chemoselective thiol conjugation and a terminal carboxylic acid for subsequent coupling or handle installation. The linker provides an approximately eleven-carbon hydrophobic spacer that helps position the reactive maleimide away from the conjugation site, often improving accessibility to cysteine-containing ligands or engineered proteins. In PROTAC and targeted protein degradation workflows, this type of maleimide–carboxylate linker is commonly used to connect a thiol-bearing binding moiety (e.g., a cysteine-functionalized ligand) to another component through stable thioether formation, while the carboxylate enables orthogonal attachment strategies such as amide coupling to a second functional group. Its value lies in enabling modular, stepwise assembly of degraders with controlled geometry and reproducible conjugation chemistry, facilitating systematic structure–activity studies and optimization of ternary-complex formation.
Structure of 57079-01-3
* For research and manufacturing use only. Not for human or clinical use.
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11-maleimidoundecanoic acid is a long-chain bifunctional linker widely used in targeted protein degradation workflows where stable conjugation chemistry is required. Its maleimide functionality enables selective coupling to thiol-bearing ligands or protein surrogates, supporting the modular assembly of PROTACs with controlled linker length and flexibility. The subsequent points provide detailed descriptions of its structural features and practical reactivity considerations for experimental preparation.
Structure: The linker contains a terminal maleimide ring conjugated to an aliphatic undecanoic acid chain. It features an electrophilic alkene within the maleimide moiety and a carboxylic acid group for further derivatization. Overall, it is an amphiphilic, flexible hydrophobic scaffold with stable covalent conjugation potential.
Reactivity: Maleimides react with nucleophilic thiols via Michael-type addition, forming a stable thioether linkage under mildly basic to neutral aqueous conditions. For PROTAC assembly, thiol presentation on the ligand or intermediate is typically achieved using reducing agents compatible with maleimide stability, followed by thiol–maleimide coupling. Solvents are commonly buffered aqueous systems or mixed organic/aqueous media to maintain solubility, while avoiding strong nucleophiles and conditions that promote maleimide hydrolysis.
* 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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