Bis-PEG13-PFP ester

 CAS No.: 1383567-59-6  Cat No.: BP-501633 4.5  

Bis-PEG13-PFP ester is a bifunctional, PEG-based linker bearing two activated pentafluorophenyl (PFP) ester termini, enabling efficient conjugation to primary amines under standard amide-forming conditions. Structurally, it comprises two polyethylene glycol chains of defined length connected to a central bis-functional scaffold, providing a flexible, hydrophilic spacer that can reduce steric bias and improve solubility of PROTAC constructs. In PROTAC design, the two PFP ester groups serve as reactive “handles” for installing or crosslinking complementary ligands (e.g., from amine-bearing warheads or E3 ligase binders) to generate stable amide linkages, thereby positioning the recognition elements at an optimized distance and orientation for ternary complex formation. This linker is valuable for researchers seeking modular, high-yield assembly of targeted protein degradation molecules, where controlled spacing and aqueous compatibility are critical for maintaining binding and promoting productive ubiquitination.

Bis-PEG13-PFP ester

Structure of 1383567-59-6

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PROTAC Linker
Molecular Formula
C₄₂H₅₆F₁₀O₁₇
Molecular Weight
1022.87

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

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IUPACName
(2,3,4,5,6-pentafluorophenyl) 3-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[3-oxo-3-(2,3,4,5,6-pentafluorophenoxy)propoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
InChI Key
WJRAPHRYVGETKA-UHFFFAOYSA-N
InChI
InChI=1S/C42H56F10O17/c43-31-33(45)37(49)41(38(50)34(31)46)68-29(53)1-3-55-5-7-57-9-11-59-13-15-61-17-19-63-21-23-65-25-27-67-28-26-66-24-22-64-20-18-62-16-14-60-12-10-58-8-6-56-4-2-30(54)69-42-39(51)35(47)32(44)36(48)40(42)52/h1-28H2
SMILES
C(COCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCC(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F

Bis-PEG13-PFP ester is a PEG-based bifunctional linker designed for constructing PROTACs through efficient amide or related coupling strategies that connect target-binding ligands to E3 ligase recruiters. Its dual activated ester functionality supports modular synthesis under mild conditions, improving synthetic flexibility and enabling systematic tuning of linker length and solubility. The subsequent points describe its structure and practical reactivity considerations for PROTAC assembly.

Structure: The linker contains a bis-PEG framework bearing two pentafluorophenyl (PFP) ester termini. It features ether-rich PEG segments that enhance hydrophilicity and conformational mobility, while the PFP groups provide activated acyl units suitable for nucleophilic substitution. The molecule is an ester-based, bifunctional coupling scaffold.

Reactivity: PFP ester linkers typically undergo acyl substitution with nucleophiles such as primary or secondary amines to form stable amide bonds, releasing pentafluorophenol as the leaving group. PROTAC synthesis commonly employs polar aprotic solvents and controlled base conditions to promote nucleophile deprotonation while minimizing side reactions. Reaction rates depend on nucleophile strength and steric environment; catalysts are generally not required, but temperature and mixing should be optimized for complete conversion.

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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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