PEG3-C4-OBn

 CAS No.: 2381196-79-6  Cat No.: BP-500165 4.5  

PEG3-C4-OBn is a bifunctional polyethylene glycol–based linker featuring a short alkyl spacer (C4) terminated with a benzyloxy (OBn) group, providing a chemically addressable handle for PROTAC assembly. The PEG3 segment imparts conformational flexibility and aqueous compatibility, while the C4 spacer helps tune the effective distance and relative orientation between the two binding modules of a PROTAC. In targeted protein degradation workflows, such linkers are used to connect a ligand for an E3 ubiquitin ligase to a ligand or warhead for the target protein, thereby enabling formation of a productive ternary complex. The benzyloxy functionality can serve as a protected alcohol motif that can be deprotected or further functionalized during synthesis, facilitating coupling to complementary electrophiles under standard organic conditions. This linker is valuable for systematic structure–activity relationship studies aimed at optimizing degradation potency, cooperativity, and physicochemical properties such as solubility and stability in experimental assays.

PEG3-C4-OBn

Structure of 2381196-79-6

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Category
PROTAC Linker
Molecular Formula
C₁₇H₂₈O₄
Molecular Weight
296.40

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

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Storage
Pure form, -20°C, 3 years; 4°C, 2 years; In solvent, -80°C, 6 months; -20°C, 1 month
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Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-(6-phenylmethoxyhexoxy)ethoxy]ethanol
InChI Key
BVCUBCXUEWSFBX-UHFFFAOYSA-N
InChI
InChI=1S/C17H28O4/c18-10-13-20-15-14-19-11-6-1-2-7-12-21-16-17-8-4-3-5-9-17/h3-5,8-9,18H,1-2,6-7,10-16H2
SMILES
C1=CC=C(C=C1)COCCCCCCOCCOCCO

PEG3-C4-OBn, is designed to provide a flexible, hydrophilic spacer that can connect two binding motifs while supporting efficient ternary complex formation. Its ethylene glycol–based segment and protected alcohol functionality help tune solubility and spatial presentation of warhead and recruiter groups. The subsequent sections describe its structural features and practical considerations for linker incorporation into targeted protein degradation constructs.

Structure: The linker contains an oligomeric polyethylene glycol segment coupled to a C4 alkyl spacer and a benzyl-protected ether alcohol terminus. It comprises ether linkages and saturated carbon frameworks, offering conformational flexibility and enhanced polarity. The benzyl ether provides a stable handle for later deprotection and functionalization.

Reactivity: For PROTAC assembly, the benzyl-protected oxygen functionality is typically carried through coupling steps using conditions compatible with benzyl ethers, then removed under standard hydrogenolysis or oxidative deprotection strategies to reveal a reactive alcohol. Subsequent formation of amide or carbamate linkages can be achieved via activated carboxylic acid derivatives. Solvent systems are selected to maintain PEG solubility and minimize side reactions.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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