Benzyl-PEG8-MS

 CAS No.: 1330059-91-0  Cat No.: BP-500504  Purity: >95% 4.5  

Benzyl-PEG8-MS is a heterobifunctional polyethylene glycol (PEG) linker featuring a benzyl-terminated end and a methanesulfonyl (mesylate) leaving group at the other terminus, enabling efficient conjugation under standard nucleophilic substitution conditions. Structurally, it contains an eight-unit PEG chain that provides water solubility, conformational flexibility, and a defined hydrophilic spacer between the PROTAC’s binding elements. In targeted protein degradation designs, this linker is used to connect a ligand-bearing nucleophile (for example, an amine or alcohol on the E3 ligase binder or target binder) to the mesylate-activated site, forming a stable ether or amine linkage while maintaining spatial separation for productive ternary complex formation. Its PEG architecture often helps reduce nonspecific interactions and improves handling in aqueous assay buffers, making it a practical building block for constructing and optimizing PROTACs and related targeted degradation conjugates.

Benzyl-PEG8-MS

Structure of 1330059-91-0

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Category
PROTAC Linker
Molecular Formula
C24H42O11S
Molecular Weight
538.65
Appearance
Transparent Liquid

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

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Purity
>95%
Appearance
Transparent Liquid
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-[2-[2-[2-[2-[2-(2-phenylmethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl methanesulfonate
Synonyms
1-Phenyl-2,5,8,11,14,17,20,23-octaoxapentacosan-25-yl methanesulfonate; 2,5,8,11,14,17,20,23-Octaoxapentacosan-25-ol, 1-phenyl-, methanesulfonate
Boiling Point
620.4±55.0°C at 760 mmHg
Density
1.2±0.1 g/cm3
InChI Key
HXGZBARQPKDPSS-UHFFFAOYSA-N
InChI
InChI=1S/C24H42O11S/c1-36(25,26)35-22-21-33-18-17-31-14-13-29-10-9-27-7-8-28-11-12-30-15-16-32-19-20-34-23-24-5-3-2-4-6-24/h2-6H,7-23H2,1H3
SMILES
CS(=O)(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCC1=CC=CC=C1

Benzyl-PEG8-MS is a polyethylene glycol-based PROTAC linker designed to connect a ligand-bearing warhead to an E3-ligase recruiting element while providing conformational flexibility and improved solubility. Its PEG architecture helps reduce steric constraints at the binding interface and can support efficient formation of productive ternary complexes. This molecule will be described in detail below, including its structural features and practical considerations for PROTAC assembly.

Structure: The linker consists of a benzyl-terminated polyethylene glycol chain incorporating a methanesulfonate (MS) leaving group at one end. It features ether linkages characteristic of PEG, a benzylic aromatic moiety, and a sulfonate ester functionality suitable for substitution chemistry.

Reactivity: The methanesulfonate end is typically used as an activated leaving group for nucleophilic substitution to install the linker onto functionalized ligands. PROTAC synthesis commonly employs mild base-promoted conditions with nucleophiles such as amines or other ligand-derived nucleophiles, using polar aprotic solvents where appropriate to maintain solubility and reaction efficiency. Reaction progress is monitored by standard analytical methods, and purification is performed to remove small-molecule byproducts.

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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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