MS-PEG3-dodecyl

 CAS No.: 2148295-99-0  Cat No.: BP-501473 4.5  

MS-PEG3-dodecyl is a heterobifunctional polyethylene glycol linker featuring a methanesulfonyl (mesyl) leaving group at one terminus and a dodecyl hydrophobic tail at the other, connected through a short PEG3 spacer. The mesylated end is designed for efficient nucleophilic substitution, enabling attachment to primary amines or other nucleophiles commonly used to functionalize PROTAC warheads or E3 ligase-binding motifs, while the dodecyl segment provides a hydrophobic handle that can enhance solubility balance, membrane/biomolecular association, or overall linker–conjugate behavior. In targeted protein degradation workflows, this linker serves as a modular “reaction-ready” bridge that allows researchers to conjugate two ligand-bearing components with controlled spacing, supporting productive ternary complex formation and minimizing steric mismatch. Its compact PEG character and hydrophobic tail make it particularly useful when optimizing linker length, flexibility, and physicochemical properties during iterative PROTAC synthesis and structure–activity studies.

MS-PEG3-dodecyl

Structure of 2148295-99-0

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PROTAC Linker
Molecular Formula
C₁₉H₄₀O₆S
Molecular Weight
396.58

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

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IUPACName
2-[2-(2-dodecoxyethoxy)ethoxy]ethyl methanesulfonate
InChI Key
CQOZFCWVYJTZJQ-UHFFFAOYSA-N
InChI
InChI=1S/C19H40O6S/c1-3-4-5-6-7-8-9-10-11-12-13-22-14-15-23-16-17-24-18-19-25-26(2,20)21/h3-19H2,1-2H3
SMILES
CCCCCCCCCCCCOCCOCCOCCOS(=O)(=O)C

This MS-PEG3-dodecyl linker is designed to provide a flexible, hydrophilic–lipophilic balance that supports efficient spatial organization between a ligand and an E3-recruiting module in PROTAC constructs. Its PEG-based segment helps reduce steric constraints and can improve solubility, while the dodecyl tail provides hydrophobic character. The detailed structural and reaction considerations are provided below.

Structure: The linker incorporates a short polyethylene glycol spacer coupled to a long-chain alkyl group, yielding an amphiphilic architecture. It contains ether linkages characteristic of PEG segments, a saturated hydrocarbon chain that contributes hydrophobic character, and a terminal mesylate (methanesulfonate) group that serves as a leaving group. Overall, it is expected to be conformationally flexible and compatible with common organic synthesis workflows.

Reactivity: For assembly, the mesylate terminus is used as an electrophilic leaving-group handle for nucleophilic substitution rather than as a carboxylic acid or amine coupling site. Reactions are commonly performed under base-assisted SN2 conditions in polar aprotic solvents with an appropriate nucleophile to form the desired C–N, C–O, C–S, or related bond. Purification by chromatography or precipitation is generally used to remove unreacted components.

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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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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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