Sulfosuccinimidyl 4,4'-azipentanoate
CAS No.: 2480172-06-1
Cat No.: BP-502163
Purity: ≥ 90%
4.5 
Sulfosuccinimidyl 4,4'-azipentanoate is a heterobifunctional, water-soluble photo-crosslinking reagent combining a sulfo-NHS ester with a diazirine group. Structurally, it contains a sulfonated N-hydroxysuccinimide ester for efficient coupling to primary amines and a 3-methyldiazirine group that can generate a reactive carbene upon UV irradiation for covalent photo-crosslinking. In PROTAC design, such linkers are used to spatially position the ligand-recruiting modules so that the ternary complex between the target-binding moiety and the E3 ligase ligand can form productively. The length and flexibility of the spacer help tune effective distance and orientation, which are critical determinants of ubiquitination efficiency and targeted protein degradation potency. Its sulfonate improves handling in aqueous buffers, facilitating reproducible synthesis of conjugates for experimental evaluation in targeted degradation workflows.
Structure of 2480172-06-1
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This PROTAC linker, Sulfosuccinimidyl 4,4’-azipentanoate, is a water-soluble NHS-ester reagent designed to enable efficient amide-bond formation with primary amines under mild conditions. Its bifunctional design supports modular assembly of targeted protein degraders by coupling to amine-bearing ligands (e.g., lysine-containing peptides or engineered affinity handles) while preserving linker flexibility for productive ternary-complex formation. Detailed structural and reactivity considerations are provided below.
Structure: The linker contains a sulfonated N-hydroxysuccinimide ester for amine acylation and a flexible azipentanoate spacer with an internal ester functionality. It features amide-forming reactive carbonyls, heteroatom-rich sulfonate for aqueous solubility, and stable covalent bonds suitable for bioconjugation workflows.
Reactivity: The NHS-ester reacts with primary amines via nucleophilic acyl substitution, forming a stable amide linkage while releasing the succinimide leaving group. Suitable conditions typically use aqueous buffers at near-neutral pH, with controlled reagent stoichiometry to minimize hydrolysis. The sulfonate improves compatibility with aqueous PROTAC assembly; no special catalysts are generally required, but freshly prepared solutions and rapid coupling are recommended to maintain reactivity.
* 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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