Propargyl-PEG1-THP

 CAS No.: 119096-95-6  Cat No.: BP-501066 4.5  

Propargyl-PEG1-THP is a heterobifunctional PROTAC linker built around a short polyethylene glycol (PEG) spacer terminating in a propargyl group and a tetrahydropyran (THP) ether handle. The PEG1 segment provides a flexible, hydrophilic connection that can reduce steric clashes between the ligand warhead and the E3-recruiting moiety, while the THP ether acts as an alcohol-protecting group that can be removed to reveal a hydroxyl group for subsequent functionalization. The propargyl group serves as a reactive alkyne for bioorthogonal conjugation strategies, most commonly copper-catalyzed azide–alkyne cycloaddition or related click-type coupling, allowing researchers to install this linker onto azide-bearing PROTAC components. In targeted protein degradation workflows, such linkers are used to tune effective intramolecular geometry and residence-time–dependent ternary complex formation, thereby supporting systematic optimization of potency and selectivity in PROTAC constructs.

Propargyl-PEG1-THP

Structure of 119096-95-6

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PROTAC Linker
Molecular Formula
C₁₀H₁₆O₃
Molecular Weight
184.23

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

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IUPACName
2-(2-prop-2-ynoxyethoxy)oxane
InChI Key
FIYFSKXDDBZITM-UHFFFAOYSA-N
InChI
InChI=1S/C10H16O3/c1-2-6-11-8-9-13-10-5-3-4-7-12-10/h1,10H,3-9H2
SMILES
C#CCOCCOC1CCCCO1

Propargyl-PEG1-THP is a PEG-based linker featuring a terminal propargyl handle and a tetrahydropyranyl (THP) protected alcohol motif, designed to support modular PROTAC assembly. Its combination of a flexible ethylene glycol segment with orthogonal functional groups enables efficient conjugation to ligands while maintaining compatibility with common synthetic sequences. The propargyl functionality supports click-type coupling strategies, and the THP group offers controlled protection that can be selectively removed when downstream functionalization is required. Detailed structural and reactivity considerations are provided below.

Structure: The linker contains a short polyethylene glycol segment that imparts conformational flexibility, connected to a propargyl group suitable for carbon–carbon bond formation via alkyne chemistry. A THP-protected oxygen atom masks an alcohol as an acetal, providing stability under mild conditions while remaining removable under acidic activation.

Reactivity: PROTAC construction using this linker commonly relies on orthogonal functional-group tactics: the terminal alkyne enables copper-catalyzed azide–alkyne cycloaddition with azide-bearing ligands under standard click conditions, typically using copper sources and polar solvents. The THP group can be deprotected using controlled acid exposure to reveal the corresponding alcohol for subsequent coupling or derivatization. Selection of solvent and temperature is guided by ligand stability and the protection/deprotection window reported for THP acetals.

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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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