Mal-PEG8-acid

 CAS No.: 1818294-46-0  Cat No.: BP-500095  Purity: ≥95% 4.5  

Mal-PEG8-acid is a heterobifunctional polyethylene glycol (PEG) linker featuring a terminal maleimide group and a carboxylic acid, with an eight-unit PEG chain that provides water solubility and conformational flexibility. The maleimide moiety is designed to undergo rapid, chemoselective Michael-type addition with thiol-containing ligands (for example, cysteine residues or thiol-functionalized warheads), enabling stable thioether conjugation under mild aqueous conditions. The terminal carboxylic acid serves as a versatile handle for further coupling strategies, such as amide-bond formation with activated carboxyl derivatives or use in coordination/derivatization workflows that support PROTAC assembly. In targeted protein degradation research, this linker helps position the E3-ligase-binding and target-binding components with reduced steric hindrance and improved solubility, which can enhance effective ternary-complex formation and overall degradation performance. It is therefore a practical reagent for constructing modular, thiol-reactive PROTACs and related conjugates for systematic structure–activity studies.

Mal-PEG8-acid

Structure of 1818294-46-0

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Category
PROTAC Linker
Molecular Formula
C23H39NO12
Molecular Weight
521.56
Related CAS
357277-61-3 (polymer) 2422928-26-3 (polymer)
Appearance
Light Yellow or White Solid

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

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Purity
≥95%
Solubility
Soluble in DCM, DMF, DMSO, Water
Appearance
Light Yellow or White Solid
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
3-[2-[2-[2-[2-[2-[2-[2-[2-(2,5-dioxopyrrol-1-yl)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
Mal-PEG8-CH2CH2COOH; Maleimide-PEG8-CH2CH2COOH; Mal-PEG8-COOH; Mal-PEG8-propionic acid; 1-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3,6,9,12,15,18,21,24-octaoxaheptacosan-27-oic acid; 4,7,10,13,16,19,22,25-Octaoxaheptacosanoic acid, 27-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-; 3,6,9,12,15,18,21,24-Octaoxaheptacosan-27-oic acid, 1-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-
Boiling Point
634.6±55.0°C at 760 mmHg
Density
1.2±0.1 g/cm3
InChI Key
KLZPPWOSICDUKQ-UHFFFAOYSA-N
InChI
InChI=1S/C23H39NO12/c25-21-1-2-22(26)24(21)4-6-30-8-10-32-12-14-34-16-18-36-20-19-35-17-15-33-13-11-31-9-7-29-5-3-23(27)28/h1-2H,3-20H2,(H,27,28)
SMILES
C1=CC(=O)N(C1=O)CCOCCOCCOCCOCCOCCOCCOCCOCCC(=O)O
ConcentrationVolumeMass1 mg5 mg10 mg
1 mM1.9173 mL9.5866 mL19.1732 mL
5 mM0.3835 mL1.9173 mL3.8346 mL
10 mM0.1917 mL0.9587 mL1.9173 mL

Mal-PEG8-acid is a PEG-based PROTAC linker featuring a maleimide handle and a terminal carboxylic acid, enabling efficient conjugation strategies used to assemble targeted protein degraders. Its flexible ethylene glycol segment improves solubility and spatial reach between binding modules, while the maleimide moiety supports selective coupling to thiol-bearing ligands. The terminal acid facilitates downstream functionalization and controlled attachment to other PROTAC components. Detailed structural and reactivity considerations are provided below.

Structure: Mal-PEG8-acid contains a maleimide electrophile connected to an extended poly(ethylene glycol) chain, terminating in a carboxylic acid. The molecule incorporates an alkene within the maleimide ring, ether linkages along the PEG backbone, and a polar acidic group, yielding a hydrophilic, conformationally flexible linker suited for PROTAC assembly.

Reactivity: The maleimide group undergoes thiol–maleimide Michael addition with cysteine or reduced thiol-containing ligands under mildly basic to neutral aqueous conditions, typically using fresh thiols to minimize side reactions. Coupling is commonly performed in buffered solvents compatible with maleimide stability, with careful control of pH and thiol stoichiometry. The carboxylic acid enables subsequent amide or ester-forming coupling to complementary PROTAC fragments using standard peptide-coupling chemistries.

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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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