Propargyl-PEG4-CH2-methyl ester

 CAS No.: 1872433-63-0  Cat No.: BP-501168  Purity: 98% 4.5  

Propargyl-PEG4-CH2-methyl ester is a polyethylene glycol–based PROTAC linker featuring a terminal propargyl (alkyne) handle and a methyl ester at the other end, with an intermediate PEG chain that provides aqueous solubility and conformational flexibility. The propargyl group enables bioorthogonal conjugation (commonly via copper-catalyzed azide–alkyne cycloaddition (CuAAC), depending on the partner), allowing researchers to attach the linker to a warhead or to a targeting ligand with minimal perturbation of binding pharmacophores. The PEG segment helps reduce nonspecific interactions and can improve the effective reach between the recruited target-binding moiety and the E3 ligase-binding component, which is central to efficient ternary complex formation. The methyl ester provides a chemically addressable functional group for subsequent hydrolysis or derivatization during linker optimization. Overall, this linker is well suited for constructing modular PROTACs and related targeted protein degradation probes where controlled conjugation and improved aqueous behavior are required.

Propargyl-PEG4-CH2-methyl ester

Structure of 1872433-63-0

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Category
PROTAC Linker
Molecular Formula
C₁₄H₂₄O₆
Molecular Weight
288.34

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

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Purity
98%
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
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Room temperature in continental US; may vary elsewhere.
IUPACName
methyl 4-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]butanoate
Synonyms
Propargyl-PEG4-(CH2)3-methyl ester
InChI Key
BUMKSEWUFKMRQT-UHFFFAOYSA-N
InChI
InChI=1S/C14H24O6/c1-3-6-17-8-10-19-12-13-20-11-9-18-7-4-5-14(15)16-2/h1H,4-13H2,2H3
SMILES
COC(=O)CCCOCCOCCOCCOCC#C

Propargyl-PEG4-CH2-methyl ester is a PEG-based, bifunctional linker designed for assembling PROTACs through orthogonal chemistries that enable efficient conjugation of ligands and controlled linker flexibility. Its propargyl handle supports click-type coupling, while the methyl ester provides a reactive site for subsequent derivatization or attachment strategies. These features make it well suited for constructing targeted protein degraders, where modular synthesis and reliable linkage formation are critical; detailed structural and reactivity considerations follow below.

Structure: The linker contains a PEG-derived hydrophilic chain providing conformational flexibility, a propargyl (alkyne) functional group for bioorthogonal coupling, and a methyl ester for electrophilic acyl reactivity. It features ether linkages along the PEG segment and ester carbonyl functionality enabling hydrolysis or substitution under appropriate conditions.

Reactivity: The propargyl group is commonly employed in copper-catalyzed azide–alkyne cycloaddition or related click methodologies using Cu(I) generated in situ, typically in polar organic/aqueous solvent systems compatible with PROTAC synthesis. The methyl ester can undergo nucleophilic acyl substitution or controlled hydrolysis to form carboxylic acids for amide or related coupling steps. Reaction design should consider solvent polarity, base selection, and compatibility with sensitive ligands.

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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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