Mal-PEG5-acid

 CAS No.: 1286755-26-7  Cat No.: BP-500100  Purity: ≥95% 4.5  

Mal-PEG5-acid is a heterobifunctional polyethylene glycol (PEG) linker featuring a terminal maleimide group for chemoselective conjugation to thiols and a terminal carboxylic acid for subsequent coupling or attachment to PROTAC scaffolds. The PEG chain length provides a flexible, hydrophilic spacer that can reduce steric interference and improve the effective reach between the ligand-binding moiety and the recruited E3 ligase component. In PROTAC design, the maleimide enables stable thioether formation with cysteine-containing ligands or thiol-functionalized intermediates, while the carboxyl group offers a handle for amide coupling to incorporate the linker into larger constructs. This linker is particularly valuable for constructing modular targeted protein degradation molecules where controlled geometry and aqueous solubility are critical for maintaining binding, promoting ternary complex formation, and supporting efficient degradation in cell-based assays.

Mal-PEG5-acid

Structure of 1286755-26-7

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Category
PROTAC Linker
Molecular Formula
C17H27NO9
Molecular Weight
389.40
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, DMSO
Appearance
Light Yellow or White Solid
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-(2,5-dioxopyrrol-1-yl)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
Mal-PEG5-CH2CH2COOH; Maleimide-PEG5-CH2CH2COOH; Mal-PEG5-COOH; Mal-PEG5-propionic acid; 1-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3,6,9,12,15-pentaoxaoctadecan-18-oic acid; 4,7,10,13,16-Pentaoxaoctadecanoic acid, 18-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-
Boiling Point
549.3±50.0°C at 760 mmHg
Density
1.2±0.1 g/cm3
InChI Key
HFYDLVZXYONWDG-UHFFFAOYSA-N
InChI
InChI=1S/C17H27NO9/c19-15-1-2-16(20)18(15)4-6-24-8-10-26-12-14-27-13-11-25-9-7-23-5-3-17(21)22/h1-2H,3-14H2,(H,21,22)
SMILES
C1=CC(=O)N(C1=O)CCOCCOCCOCCOCCOCCC(=O)O
ConcentrationVolumeMass1 mg5 mg10 mg
1 mM2.5681 mL12.8403 mL25.6805 mL
5 mM0.5136 mL2.5681 mL5.1361 mL
10 mM0.2568 mL1.2840 mL2.5681 mL

This Mal-PEG5-acid linker is designed for efficient conjugation in targeted protein degradation workflows, enabling robust attachment of ligands to generate PROTAC constructs. Its PEG-based spacer provides favorable solubility and conformational flexibility, while the maleimide functionality supports selective coupling to thiol-bearing partners under mild conditions. The resulting linkages can improve the practical assembly of degraders and support systematic structure–activity exploration; the following sections describe its structure and reactivity in detail below.

Structure: Mal-PEG5-acid comprises a maleimide electrophile linked to a poly(ethylene glycol) spacer terminating in a carboxylic acid. The maleimide ring contains activated double bonds for thiol addition, while the PEG chain provides ether-rich, flexible connectivity. The carboxyl group offers an anionic handle for downstream coupling and salt formation.

Reactivity: The maleimide group reacts with sulfhydryl-containing nucleophiles via a Michael-type addition to form a stable thioether linkage. Suitable conditions typically use aqueous or mixed aqueous buffers at near-neutral pH, with controlled temperature and exclusion of competing thiols. Common solvents include water, buffered aqueous media, and compatible co-solvents used for solubilizing ligands. No specialized catalysts are generally required; reaction rate and selectivity depend on thiol availability and buffer composition.

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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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