1-(p-azidosalicylamido)-4-(iodoacetamido)butane

 CAS No.: 183006-87-3  Cat No.: BP-502169 4.5  

1-(p-Azidosalicylamido)-4-(iodoacetamido)butane is a bifunctional PROTAC linker featuring an azide-containing salicylamide moiety and a terminal iodoacetamide electrophile separated by a short aliphatic chain. The iodoacetamide group is designed to form a stable thioether with nucleophilic cysteine residues on a target-binding ligand or engineered protein-capture component, enabling covalent attachment within targeted degradation constructs. In parallel, the azido functionality provides a versatile handle for bioorthogonal derivatization or for downstream conjugation strategies, allowing researchers to tune the spatial relationship between the recruitment element and the E3-ligase or binding module. The p-azidosalicylamide motif can contribute favorable hydrogen-bonding and aromatic positioning that supports effective ternary-complex formation in PROTAC architectures. This linker is therefore valuable for experiments requiring controlled conjugation geometry, covalent tethering, and modular assembly of targeted degradation molecules for mechanistic and optimization studies.

1-(p-azidosalicylamido)-4-(iodoacetamido)butane

Structure of 183006-87-3

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PROTAC Linker
Molecular Formula
C13H16IN5O3
Molecular Weight
417.3

* For research and manufacturing use only. Not for human or clinical use.

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IUPACName
4-azido-2-hydroxy-N-[4-[(2-iodoacetyl)amino]butyl]benzamide
Synonyms
ASIB; 1-(4-Azidosalicylamido)-4-(iodoacetamido)butane
InChI Key
NXLBAOLUZNMYKG-UHFFFAOYSA-N
InChI
InChI=1S/C13H16IN5O3/c14-8-12(21)16-5-1-2-6-17-13(22)10-4-3-9(18-19-15)7-11(10)20/h3-4,7,20H,1-2,5-6,8H2,(H,16,21)(H,17,22)
SMILES
C1=CC(=C(C=C1N=[N+]=[N-])O)C(=O)NCCCCNC(=O)CI

This PROTAC linker, 1-(p-azidosalicylamido)-4-(iodoacetamido)butane, is designed to provide orthogonal functional handles for stepwise assembly of targeted protein degraders. Its bifunctional design supports reliable conjugation strategies that preserve key binding motifs while enabling efficient formation of the final PROTAC scaffold. The azide and iodoacetamide functionalities offer practical modularity for coupling to ligands and for subsequent click-style or nucleophile-driven steps. Detailed structural and reactivity considerations are provided below.

Structure: The linker contains an amide-linked butyl spacer bearing an azidosalicylamide aromatic fragment and a terminal iodoacetamide electrophile. It features stable amide and aromatic ether-like coordination motifs, plus an azide group suitable for bioorthogonal transformations. Overall, it presents a polar, hydrogen-bonding-rich scaffold with a reactive alkyl halide moiety.

Reactivity: The iodoacetamide group is suitable for nucleophilic substitution with thiol-containing ligands or cysteine-directed conjugation under conditions that maintain electrophile reactivity while limiting side reactions. The azide handle enables azide-compatible coupling approaches, including copper-free or copper-assisted azide–alkyne cycloaddition depending on the ligand set. Typical assembly employs inert atmosphere, appropriate buffering, and controlled pH to balance stability of amide linkages and electrophile integrity.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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