PEG20-Tos

 CAS No.: 2179113-08-5  Cat No.: BP-501265 4.5  

PEG20-Tos is a polyethylene glycol–based linker bearing a tosyl (tosylate) leaving group, providing a chemically versatile handle for PROTAC assembly. Structurally, it consists of a PEG chain of approximately twenty ethylene glycol units terminated with a sulfonate ester, which imparts aqueous solubility, conformational flexibility, and reduced nonspecific hydrophobic interactions. In targeted protein degradation designs, PEG linkers are commonly used to spatially tune the relative orientation and effective reach between the ligand-binding moiety (e.g., an E3 ligase binder) and the recruited protein target or second ligand. The tosylate functionality enables efficient nucleophilic substitution with amines or other suitable nucleophiles, allowing researchers to conjugate PEG20-Tos to functional groups on PROTAC components under standard organic synthesis conditions. This linker is valuable for optimizing linker length and attachment chemistry, improving synthetic modularity, and supporting systematic structure–activity relationship studies in PROTAC and related targeted degradation research.

PEG20-Tos

Structure of 2179113-08-5

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PROTAC Linker
Molecular Formula
C₄₇H₈₈O₂₃S
Molecular Weight
1053.25

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

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IUPACName
2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate
InChI Key
ZWCZGEMXBISIJU-UHFFFAOYSA-N
InChI
InChI=1S/C47H88O23S/c1-46-2-4-47(5-3-46)71(49,50)70-45-44-69-43-42-68-41-40-67-39-38-66-37-36-65-35-34-64-33-32-63-31-30-62-29-28-61-27-26-60-25-24-59-23-22-58-21-20-57-19-18-56-17-16-55-15-14-54-13-12-53-11-10-52-9-8-51-7-6-48/h2-5,48H,6-45H2,1H3
SMILES
CC1=CC=C(C=C1)S(=O)(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO

This PROTAC linker, PEG20-Tos, is designed to provide a biocompatible polyethylene glycol (PEG) spacer with a tosylate leaving group, enabling efficient attachment of ligands and controlled spatial presentation in targeted protein degradation constructs. Its flexible hydrophilic character can improve solubility and help tune linker length and conformational freedom, supporting robust formation of PROTAC intermediates. The following sections describe the linker’s structure and practical reactivity considerations in PROTAC synthesis.

Structure: PEG20-Tos comprises a polyethylene glycol chain terminating in a tosylate (p-toluenesulfonate) group. The linker features ether linkages within the PEG segment and a sulfonate ester at the reactive terminus. These functionalities confer hydrophilicity, chemical stability under mild conditions, and a good leaving group for substitution reactions.

Reactivity: The tosylate group is suited for nucleophilic substitution to install PROTAC-binding motifs, typically via SN2-type displacement using appropriate nucleophiles such as amines or oxygen-centered nucleophiles. Linker coupling is commonly performed under anhydrous, inert or controlled atmospheres to minimize side reactions, using polar aprotic solvents compatible with PEG systems. Reaction progress is monitored by standard analytical methods, and purification is typically optimized to remove sulfonate byproducts and unreacted starting materials.

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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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