Propargyl-PEG5-Br

 CAS No.: 1287660-83-6  Cat No.: BP-501162 4.5  

Propargyl-PEG5-Br is a heterobifunctional polyethylene glycol (PEG) linker featuring a terminal propargyl group for alkyne-based conjugation and a bromide leaving group at the opposite end for nucleophilic substitution. The PEG5 chain provides a hydrophilic, flexible spacer that can reduce steric interference and improve the effective presentation of the two reactive termini when assembling PROTACs. In targeted protein degradation workflows, this linker can first undergo SN2 substitution at the alkyl bromide with a suitable nucleophile, while the terminal alkyne can be coupled to an azide-bearing partner by CuAAC, enabling modular synthesis of PROTAC architectures. The propargyl handle supports copper-catalyzed azide–alkyne cycloaddition or related click chemistries, while the bromide end facilitates installation onto nucleophile-functionalized fragments. Its utility lies in enabling systematic variation of linker length and attachment geometry, which is critical for optimizing ternary complex formation, cellular permeability, and degradation potency in PROTAC research.

Propargyl-PEG5-Br

Structure of 1287660-83-6

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PROTAC Linker
Molecular Formula
C₁₃H₂₃BrO₅
Molecular Weight
339.22

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

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IUPACName
3-[2-[2-[2-[2-(2-bromoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]prop-1-yne
InChI Key
LHPVARBMQIBDST-UHFFFAOYSA-N
InChI
InChI=1S/C13H23BrO5/c1-2-4-15-6-8-17-10-12-19-13-11-18-9-7-16-5-3-14/h1H,3-13H2
SMILES
C#CCOCCOCCOCCOCCOCCBr

Propargyl-PEG5-Br is a PEG-based bromoalkyl linker designed to support modular PROTAC synthesis by enabling efficient conjugation between targeting ligands and E3-recruiting or warhead components. Its ether-rich, flexible backbone helps maintain productive spatial orientation and can improve overall construct solubility in common organic and mixed solvent systems. The propargyl handle further supports orthogonal click-type coupling strategies, while the bromide provides a convenient electrophilic site for nucleophilic substitution. Detailed structural and reactivity considerations are provided below.

Structure: The linker comprises a poly(ethylene glycol) chain terminating in a propargyl group and a terminal bromide. It contains ether linkages within the PEG segment and a carbon–carbon triple bond at the propargyl terminus, with a primary C–Br electrophile suitable for substitution chemistry.

Reactivity: The terminal bromide can undergo nucleophilic substitution with appropriate nucleophiles (for example, amines or thiolates) under standard alkylation conditions, typically using polar aprotic solvents and base control to favor substitution. The propargyl group enables copper-catalyzed azide–alkyne cycloaddition or related alkyne click conjugations, following established PROTAC assembly practices where catalyst choice, solvent, and ligand stability are optimized to preserve functional groups during coupling.

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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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