Mal-PEG12-propionic acid

 CAS No.: 2445165-75-1  Cat No.: BP-500437  Purity: ≥95% 4.5  

Mal-PEG12-propionic acid is a heterobifunctional PEG-based linker featuring a maleimide group for rapid, chemoselective conjugation to thiols, coupled to a terminal propionic acid handle that can be used for subsequent coupling, immobilization, or further PROTAC assembly. Structurally, it provides a long, flexible poly(ethylene glycol) chain that acts as a spacer, improving solubility and reducing steric interference between the “warhead” and the recruiting ligand or other functional moieties. In targeted protein degradation workflows, the maleimide enables site-specific attachment to cysteine-containing proteins, peptides, or thiol-bearing building blocks, while the carboxylic acid functionality supports controlled linkage to complementary partners through standard amide-forming chemistries. This linker is valuable for constructing degraders and related conjugates where maintaining productive geometry and minimizing nonspecific aggregation are critical for efficient ternary-complex formation and downstream degradation readouts.

Mal-PEG12-propionic acid

Structure of 2445165-75-1

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Category
PROTAC Linker
Molecular Formula
C31H55NO16
Molecular Weight
697.77
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%
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-[2-[2-[2-(2,5-dioxopyrrol-1-yl)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
Mal-PEG12-CH2CH2COOH; Maleimide-PEG12-CH2CH2COOH; Mal-PEG12-COOH; Mal-PEG12-acid; 4,7,10,13,16,19,22,25,28,31,34,37-Dodecaoxanonatriacontanoic acid, 39-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-; 1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3,6,9,12,15,18,21,24,27,30,33,36-dodecaoxanonatriacontan-39-oic acid; 3,6,9,12,15,18,21,24,27,30,33,36-Dodecaoxanonatriacontan-39-oic acid, 1-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-; 39-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)-4,7,10,13,16,19,22,25,28,31,34,37-dodecaoxanonatriacontanoic acid
Boiling Point
740.2±60.0°C at 760 mmHg
Density
1.188±0.1 g/cm3
InChI Key
FRRHLQYEWMQTLF-UHFFFAOYSA-N
InChI
InChI=1S/C31H55NO16/c33-29-1-2-30(34)32(29)4-6-38-8-10-40-12-14-42-16-18-44-20-22-46-24-26-48-28-27-47-25-23-45-21-19-43-17-15-41-13-11-39-9-7-37-5-3-31(35)36/h1-2H,3-28H2,(H,35,36)
SMILES
C1=CC(=O)N(C1=O)CCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCC(=O)O

Mal-PEG12-propionic acid is a polyethylene glycol (PEG)-based bifunctional linker designed for constructing targeted protein degradation (PROTAC) molecules. Its maleimide handle enables efficient conjugation to thiol-containing ligands, while the terminal carboxylic acid supports subsequent coupling or formulation strategies. The PEG segment provides aqueous solubility and conformational flexibility, which can improve linker accessibility and degradation performance in PROTAC workflows. The structure and reactivity considerations are described in detail below.

Structure: Mal-PEG12-propionic acid contains a maleimide moiety connected to a PEG chain terminating in a propionic acid group. It features an electrophilic alkene within the maleimide ring, an ether-rich PEG backbone, and a carboxylic acid for controlled functionalization. The linker is typically water-compatible and flexible due to the PEG segment.

Reactivity: The maleimide group reacts with primary or secondary thiols via a Michael-type addition, forming a stable thioether linkage under mildly basic, aqueous-compatible conditions. For PROTAC assembly, thiolated targeting ligands are commonly generated or introduced prior to coupling, while the carboxylic acid can be used in amide-forming coupling steps using standard peptide-coupling chemistries. Solvent systems are typically chosen to balance thiol stability and maleimide reactivity, and inert handling is often used to limit thiol oxidation.

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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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