Mal-PEG4-acid

 CAS No.: 518044-41-2  Cat No.: BP-500120  Purity: >95% 4.5  

Mal-PEG4-acid is a heterobifunctional polyethylene glycol linker bearing a maleimide electrophile and a terminal carboxylic acid, enabling controlled conjugation chemistry for targeted protein degradation platforms. The PEG4 chain provides aqueous solubility and conformational spacing, while the maleimide moiety reacts selectively with thiol-containing groups (for example, cysteine residues or thiol-functionalized ligands) via Michael-type addition to form a stable thioether linkage. The carboxylic acid handle can be used for subsequent amide coupling or other carbodiimide-mediated functionalization, allowing integration of the linker into PROTAC architectures where a ligand for an E3 ligase or a target-binding warhead must be precisely positioned relative to the degradation-driving interface. In PROTAC research, such linkers help tune effective molarity, reduce steric hindrance, and improve conjugate stability in biological media, facilitating systematic structure–activity studies and optimization of ternary complex formation.

Mal-PEG4-acid

Structure of 518044-41-2

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Category
PROTAC Linker
Molecular Formula
C15H23NO8
Molecular Weight
345.35
Related CAS
357277-61-3 (polymer) 2422928-26-3 (polymer)
Appearance
Pale Yellow Oily Liquid

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

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Purity
>95%
Solubility
Soluble in DCM, Water
Appearance
Pale Yellow Oily Liquid
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
3-[2-[2-[2-[2-(2,5-dioxopyrrol-1-yl)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
Mal-PEG4-CH2CH2COOH; Maleimide-PEG4-CH2CH2COOH; Mal-PEG4-COOH; Mal-PEG4-propionic acid; 1-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3,6,9,12-tetraoxapentadecan-15-oic acid; 15-maleinimido-4,7,10,13-tetroxapentadecanoic acid; 3,6,9,12-Tetraoxapentadecan-15-oic acid, 1-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-
Boiling Point
520.1±50.0 °C at 760 mmHg
Density
1.268±0.06 g/cm3 (Predicted)
InChI Key
BTFZSOVKVDCKQD-UHFFFAOYSA-N
InChI
InChI=1S/C15H23NO8/c17-13-1-2-14(18)16(13)4-6-22-8-10-24-12-11-23-9-7-21-5-3-15(19)20/h1-2H,3-12H2,(H,19,20)
SMILES
C1=CC(=O)N(C1=O)CCOCCOCCOCCOCCC(=O)O
ConcentrationVolumeMass1 mg5 mg10 mg
1 mM2.8956 mL14.4781 mL28.9561 mL
5 mM0.5791 mL2.8956 mL5.7912 mL
10 mM0.2896 mL1.4478 mL2.8956 mL

Mal-PEG4-acid is a polyethylene glycol-based PROTAC linker bearing a maleimide functionality and a terminal carboxylic acid. It enables chemoselective conjugation to thiol-containing ligands while providing a hydrophilic spacer to tune solubility, reduce nonspecific interactions, and help position recruited binding motifs within PROTAC constructs. The maleimide handle supports robust assembly of targeted protein degraders, and the terminal acid provides a convenient functional group for further derivatization; detailed structural and reactivity considerations are provided below.

Structure: The linker comprises a maleimide electrophile connected to a short PEG chain terminating in a carboxylic acid. It contains an activated alkene within the maleimide ring and an ester-free ether-rich PEG segment. The presence of polar ether and acid groups supports water compatibility and flexible conformations.

Reactivity: Maleimides react selectively with thiols via Michael-type addition to form a stable thioether linkage, typically under mildly basic, aqueous-compatible conditions that preserve maleimide reactivity while controlling thiol oxidation. Assembly commonly uses thiol-bearing ligands or cysteine-reactive precursors. Solvent systems are chosen to balance solubility of PEG and reactants, and reaction progress is monitored to minimize hydrolysis or side reactions.

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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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