Bis-PEG5-PFP ester

 CAS No.: 1334177-78-4  Cat No.: BP-500624 4.5  

Bis-PEG5-PFP ester is a bifunctional polyethylene glycol (PEG) linker featuring two PEG5 chains terminated with pentafluorophenyl (PFP) ester groups. The PFP ester moieties are activated carboxylate derivatives that readily undergo nucleophilic acyl substitution with primary amines, enabling efficient conjugation under mild, commonly used bioconjugation conditions. In PROTAC and targeted protein degradation workflows, this linker is valuable for connecting an E3 ligase-binding ligand (or other targeting module) to a second functional component such as a second ligand, a solubilizing handle, or a reactive intermediate, while the PEG segments provide conformational flexibility and improved aqueous compatibility. The bis-functional design supports controlled, stoichiometric assembly of heterobifunctional constructs and can help reduce aggregation and nonspecific hydrophobic interactions during synthesis and biological testing.

Bis-PEG5-PFP ester

Structure of 1334177-78-4

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Category
PROTAC Linker
Molecular Formula
C₂₆H₂₄F₁₀O₉
Molecular Weight
670.45
Appearance
Liquid

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

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Liquid
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
(2,3,4,5,6-pentafluorophenyl) 3-[2-[2-[2-[2-[3-oxo-3-(2,3,4,5,6-pentafluorophenoxy)propoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
Bis-PEG5-PFP ester; 1334177-78-4; PFP-PEG5-PFP; Bis(perfluorophenyl) 4,7,10,13,16-pentaoxanonadecane-1,19-dioate; bis(perfluorophenyl) 4,7,10,13,16-pentaoxanonadecanedioate; BIS-PEG5-PFPESTER; Bis-dPEG(R)5-PFP ester; SCHEMBL11912114
InChI Key
PVXXABBOISIWMS-UHFFFAOYSA-N
InChI
InChI=1S/C26H24F10O9/c27-15-17(29)21(33)25(22(34)18(15)30)44-13(37)1-3-39-5-7-41-9-11-43-12-10-42-8-6-40-4-2-14(38)45-26-23(35)19(31)16(28)20(32)24(26)36/h1-12H2
SMILES
C(COCCOCCOCCOCCOCCC(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F

Bis-PEG5-PFP ester, is designed to provide a flexible polyethylene glycol spacer while presenting activated pentafluorophenyl (PFP) ester handles for efficient conjugation. Its PEG architecture supports improved solubility and conformational adaptability in targeted protein degradation constructs. The PFP ester functionality enables reliable amide-bond formation with nucleophilic partners commonly used in PROTAC assembly.

Structure: The molecule contains two PEG-based arms terminating in pentafluorophenyl ester groups, connected through ether linkages that confer flexibility. The PFP ester moieties incorporate an electron-withdrawing aromatic ring, enhancing electrophilicity at the carbonyl. Overall, the linker is expected to be polar and water-compatible due to the PEG chains.

Reactivity: PFP esters typically react with primary amines to form stable amide bonds via nucleophilic acyl substitution. PROTAC assembly commonly uses mild base conditions to generate the amine nucleophile, with polar organic solvents or buffered aqueous mixtures to maintain solubility. No special catalysts are generally required; however, controlling pH and stoichiometry helps minimize hydrolysis. The activated ester should be handled under conditions that limit competing water-mediated ester degradation.

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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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