6-Maleimidocaproic acid-PFP ester
CAS No.: 692739-25-6
Cat No.: BP-501352
4.5 
6-Maleimidocaproic acid-PFP ester is a bifunctional PROTAC linker reagent combining a maleimide group with a pentafluorophenyl (PFP) ester for efficient, orthogonal conjugation. The maleimide moiety enables selective coupling to thiol-containing handles (for example, cysteine residues or engineered thiol tags) via stable thioether formation, while the PFP ester serves as an activated carboxylate that reacts with primary amines to form amide bonds. Structurally, it provides a flexible caproic acid spacer that helps tune the distance and relative orientation between the two conjugation sites, which is critical for preserving binding affinity of the recruited ligand and the degrader payload in ternary-complex formation. In targeted protein degradation workflows, this linker is valuable for assembling PROTACs from thiol- and amine-functionalized components, facilitating modular synthesis, purification, and systematic structure–activity optimization.
Structure of 692739-25-6
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This PROTAC linker, 6-Maleimidocaproic acid-PFP ester, is designed to provide a robust chemical handle for building targeted protein degraders. Its bifunctional character enables efficient conjugation to thiol-bearing ligands while maintaining a flexible spacer that can support productive ternary complex formation. The PFP ester functionality supports reliable coupling under standard amide-forming conditions, and the maleimide moiety supports selective thiol capture. Detailed structural and reactivity considerations are provided below.
Structure: The molecule contains a caproic acid-derived flexible aliphatic chain, a maleimide electrophile for thiol addition, and a pentafluorophenyl (PFP) ester that is activated toward nucleophilic acyl substitution. It features conjugated imide carbonyls and an activated aromatic leaving group, supporting controlled bioconjugation.
Reactivity: For PROTAC assembly, the PFP ester is typically used to couple to primary amines to form stable amide bonds via nucleophilic acyl substitution, often under mildly basic aqueous or mixed solvent conditions. The maleimide group can then react with cysteine or other thiol-containing partners through Michael-type addition, commonly in buffered solutions that favor thiol availability. No specialized catalysts are generally required; careful control of pH and thiol stoichiometry helps preserve selectivity.
* 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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