Mal-amido-PEG3-acid

 CAS No.: 2055353-75-6  Cat No.: BP-500221 4.5  

Mal-amido-PEG3-acid is a heterobifunctional polyethylene glycol linker featuring a maleimide-bearing amide terminus and a terminal carboxylic acid, with a short PEG3 chain that provides aqueous solubility and conformational flexibility. In PROTAC and targeted protein degradation workflows, the maleimide group enables selective conjugation to thiol-containing ligands (e.g., cysteine residues or thiol-functionalized warheads) through stable thioether bond formation, while the carboxylic acid handle can be used for subsequent coupling to complementary components such as another ligand, a targeting moiety, or a scaffold via amide or ester-forming chemistry. The PEG spacer helps reduce steric hindrance and can improve productive orientation between the recruited protein-binding element and the E3 ligase binder, thereby supporting formation of an effective ternary complex. This linker is therefore valuable for constructing modular, water-compatible PROTACs and for systematic optimization of linker length and attachment chemistry in degradation studies.

Mal-amido-PEG3-acid

Structure of 2055353-75-6

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PROTAC Linker
Molecular Formula
C₁₆H₂₄N₂O₈
Molecular Weight
372.37

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

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IUPACName
3-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethoxy]propanoic acid
InChI Key
VRSINYAEWCLYBF-UHFFFAOYSA-N
InChI
InChI=1S/C16H24N2O8/c19-13(3-6-18-14(20)1-2-15(18)21)17-5-8-25-10-12-26-11-9-24-7-4-16(22)23/h1-2H,3-12H2,(H,17,19)(H,22,23)
SMILES
C1=CC(=O)N(C1=O)CCC(=O)NCCOCCOCCOCCC(=O)O

Mal-amido-PEG3-acid is a polyethylene glycol-based PROTAC linker featuring a maleimide-derived amide functionality and a terminal carboxylic acid. It is designed to support modular assembly of targeted protein degraders by enabling stable conjugation to thiol-containing ligands and by providing a hydrophilic, flexible spacer that can improve effective ternary complex formation. The structure and reactivity considerations for constructing PROTACs with this linker are described in detail below.

Structure: The linker combines a PEG chain for conformational flexibility with an amide-linked maleimide motif and a terminal carboxylic acid. It contains amide and ether linkages, with a maleimide electrophilic double bond suitable for selective thiol addition. Overall, it is highly polar and water-compatible.

Reactivity: The maleimide group undergoes Michael-type addition with thiols under mildly basic to neutral aqueous conditions, forming a stable thioether linkage. Carboxylic acid functionality can be activated for amide coupling to amine-bearing partners using standard coupling reagents and appropriate bases. Solvent systems commonly include aqueous buffers with compatible co-solvents, and reaction progress is typically monitored by analytical methods to minimize hydrolysis or side reactions.

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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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Historical Records: 5-Maleimido-2-hydraziniumpyridine hydrochloride | HO-PEG14-OH | TAMRA-PEG4-acid | Aminooxy-PEG2-azide | m-PEG10-Br | Propargyl-PEG25-acid | HS-PEG7-CH2CH2COOH | HO-PEG24-CH2CH2COOH | DSPE-PEG5-azide | TCO-PEG6-amine | Mal-amido-PEG3-acid

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