Mal-PEG2-PFP

 CAS No.: 1807512-47-5  Cat No.: BP-501337  Purity: ≥98% 4.5  

Mal-PEG2-PFP is a bifunctional, short-chain polyethylene glycol (PEG) linker designed for PROTAC and targeted protein degradation workflows. Structurally, it combines a maleimide (Mal) group for rapid, chemoselective conjugation to thiol-containing ligands or cysteine residues, with a terminal perfluorophenyl (PFP) ester handle that can form stable amide bonds with primary amines under standard coupling conditions. The PEG2 spacer provides modest hydrophilicity and conformational flexibility, which can help reduce steric clashes and improve productive ternary-complex formation between the ligand-bearing “warhead” and the E3 ligase-recruiting moiety. In PROTAC construction, this linker enables modular assembly by sequentially attaching one component through thiol–maleimide chemistry and the other through amide coupling, yielding degraders with defined connectivity and controlled linker length. Its utility lies in facilitating reproducible synthesis and optimization of linker geometry, supporting systematic structure–activity studies in targeted degradation research.

Mal-PEG2-PFP

Structure of 1807512-47-5

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Category
PROTAC Linker
Molecular Formula
C17H14F5NO6
Molecular Weight
423.29
Appearance
Soild powder

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

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Purity
≥98%
Solubility
Soluble in DCM, DMF, DMSO
Appearance
Soild powder
Storage
Store at 2-8°C
Shipping
Room temperature
IUPACName
(2,3,4,5,6-pentafluorophenyl) 3-[2-[2-(2,5-dioxopyrrol-1-yl)ethoxy]ethoxy]propanoate
Synonyms
Mal-PEG2-PFP ester; Perfluorophenyl 3-(2-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy)ethoxy)propanoate; Perfluorophenyl 3-(2-(2-(2,5-dioxo-2H-pyrrol-1(5H)-yl)ethoxy)ethoxy)propanoate; Propanoic acid, 3-[2-[2-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)ethoxy]ethoxy]-, 2,3,4,5,6-pentafluorophenyl ester
Boiling Point
493.1±45.0°C at 760 mmHg
Density
1.5±0.1 g/cm3
InChI Key
YMKYKJKJMZSGEN-UHFFFAOYSA-N
InChI
InChI=1S/C17H14F5NO6/c18-12-13(19)15(21)17(16(22)14(12)20)29-11(26)3-5-27-7-8-28-6-4-23-9(24)1-2-10(23)25/h1-2H,3-8H2
SMILES
C1=CC(=O)N(C1=O)CCOCCOCCC(=O)Oc2c(c(c(c(c2F)F)F)F)F

Mal-PEG2-PFP is a bifunctional PROTAC linker designed to connect a maleimide-bearing handle with a reactive pentafluorophenyl ester for efficient conjugation workflows. Its PEG-based spacer supports productive ternary-complex formation by improving solubility and conformational flexibility, while the complementary electrophile pairs enable straightforward assembly of targeted degradation constructs. The detailed structural and reactivity considerations for building PROTACs with this linker are provided below.

Structure: Mal-PEG2-PFP contains a maleimide moiety for selective thiol coupling and a pentafluorophenyl ester for acyl-transfer chemistry, separated by a short PEG spacer. The molecule features an ether-rich, flexible backbone and aromatic electron-poor activation that enhances ester reactivity.

Reactivity: For PROTAC synthesis, the maleimide typically reacts with nucleophilic thiols under mildly basic to neutral aqueous/organic conditions, forming a stable thioether linkage via Michael-type addition. The pentafluorophenyl ester is suited for amide-bond formation with primary amines or other suitable nucleophiles, often using polar aprotic solvents and controlled pH to balance electrophile stability and nucleophile availability. Commonly, sequential coupling is performed to minimize cross-reactivity between handles.

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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 ╳
g/mol
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