m-PEG6-Tos

 CAS No.: 155887-96-0  Cat No.: BP-501398 4.5  

m-PEG6-Tos is a methoxy-terminated polyethylene glycol (PEG) linker bearing a tosyl (tosylate) functional group, providing a flexible, water-compatible chain of defined length for PROTAC synthesis. Structurally, it combines a PEG spacer that reduces steric constraints and improves solubility with a tosylate leaving group that enables efficient nucleophilic substitution or coupling to introduce the linker into PROTAC constructs. In targeted protein degradation design, this linker serves as a “molecular spacer” that spatially tunes the relative positioning of the E3 ligase ligand and the target-binding ligand, thereby influencing ternary complex formation and degradation potency. The PEG segment can also mitigate aggregation and improve handling during conjugation and downstream assays. As a modular intermediate, m-PEG6-Tos is valuable for researchers optimizing linker length and attachment chemistry in PROTACs, facilitating systematic structure–activity relationship studies while maintaining robust synthetic accessibility.

m-PEG6-Tos

Structure of 155887-96-0

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PROTAC Linker
Molecular Formula
C₂₀H₃₄O₉S
Molecular Weight
450.54

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

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IUPACName
2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate
InChI Key
IULJXDNZSJIPDE-UHFFFAOYSA-N
InChI
InChI=1S/C20H34O9S/c1-19-3-5-20(6-4-19)30(21,22)29-18-17-28-16-15-27-14-13-26-12-11-25-10-9-24-8-7-23-2/h3-6H,7-18H2,1-2H3
SMILES
CC1=CC=C(C=C1)S(=O)(=O)OCCOCCOCCOCCOCCOCCOC

m-PEG6-Tos is a PEG-based linker bearing a tosylate (Tos) leaving group designed for efficient conjugation in PROTAC assembly workflows. Its ether-rich PEG segment provides conformational flexibility and can improve solubility and handleability of bifunctional constructs, while the tosylate enables nucleophilic substitution to install functional groups on target-binding moieties. The points below describe its structural features and practical reactivity considerations for constructing PROTACs.

Structure: The linker consists of an oligo(ethylene glycol) chain connected to an aromatic tosylate group. It contains ether linkages along the PEG backbone and a sulfonate ester at the terminus, providing a stable scaffold with a good balance of polarity and leaving-group reactivity.

Reactivity: The tosylate group is suitable for substitution reactions with nucleophiles such as amines or alcoholates under standard organic synthesis conditions. Conjugation is typically performed via SN2-type displacement, with base-assisted activation of the nucleophile. Common approaches use polar aprotic solvents and mild temperatures to preserve sensitive binding ligands, and the reaction is monitored to optimize conversion and minimize side reactions.

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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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