m-PEG3-S-PEG3-Boc

 CAS No.: 2055040-96-3  Cat No.: BP-500765 4.5  

m-PEG3-S-PEG3-Boc is a heterobifunctional PEG linker featuring a methoxy-capped terminus at one end, a thioether linkage within the chain, and a Boc-protected carboxylate at the other end. The methoxy group provides a stable, non-reactive capping functionality that prevents unwanted side reactions at this terminus, while the Boc-protected carboxylate, upon deprotection, yields a free carboxylic acid for selective amide coupling with amine-containing target protein ligands or E3 ubiquitin ligase-recruiting moieties. The incorporated thioether linkage introduces a sulfur atom into the PEG backbone, which can influence the conformational properties, lipophilicity, and metabolic stability of the linker relative to all-oxygen PEG analogs. Thioether-containing linkers have been explored in PROTAC design as they may modulate linker flexibility and interact favorably with hydrophobic regions on target proteins or E3 ligases, potentially contributing to stabilizing contacts within the ternary complex. The symmetric PEG segments flanking the thioether provide balanced hydrophilicity and conformational freedom. Researchers utilize this linker to investigate how heteroatom incorporation within the PEG backbone affects degradation efficiency, selectivity, and the physicochemical properties of PROTAC molecules in targeted protein degradation studies.

m-PEG3-S-PEG3-Boc

Structure of 2055040-96-3

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PROTAC Linker
Molecular Formula
C₂₀H₄₀O₈S
Molecular Weight
440.59

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

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IUPACName
tert-butyl 3-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethylsulfanyl]ethoxy]ethoxy]ethoxy]propanoate
InChI Key
HPUREYBEJCEQQQ-UHFFFAOYSA-N
InChI
InChI=1S/C20H40O8S/c1-20(2,3)28-19(21)5-6-23-9-10-25-12-14-27-16-18-29-17-15-26-13-11-24-8-7-22-4/h5-18H2,1-4H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCSCCOCCOCCOC

This m-PEG3-S-PEG3-Boc linker is designed to connect PROTAC-binding modules through a PEG-based, thioether-containing scaffold that supports conformational flexibility and improved solubility. Its Boc-protected functionality enables controlled downstream functionalization, facilitating the modular assembly of targeted protein degraders. The linker’s architecture is well suited for constructing conjugates that maintain productive geometry between ligands and the recruited E3 machinery.

Structure: The linker comprises PEG oligomer segments linked through a thioether (sulfide) and incorporates a Boc-protected functional group. It contains ether linkages within the PEG chains, flexible C–O and C–S connectivity, and a carbamate motif from the Boc group. Overall, it is expected to be polar and water-compatible.

Reactivity: Boc-protected sites are typically introduced or manipulated using acid-mediated deprotection, followed by coupling to appropriate ligand handles. The thioether linkage is generally stable under mild conditions, supporting stepwise PROTAC synthesis. For conjugation, standard amide or carbamate-forming chemistries can be applied after deprotection, using common coupling reagents and polar aprotic solvents, while maintaining conditions that preserve PEG integrity and the sulfide linkage.

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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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