Mal-NH-PEG3-NH-Mal

 CAS No.: 1008402-47-8  Cat No.: BP-501250  Purity: >97% 4.5  

Mal-NH-PEG3-NH-Mal is a bifunctional polyethylene glycol linker bearing two maleimide groups at its termini and a short, flexible PEG spacer that provides controlled distance and solubility. The maleimide handles undergo selective Michael-type addition with thiol-containing nucleophiles (for example, cysteine residues or reduced thiols on targeting ligands), enabling efficient conjugation under mild aqueous conditions. In PROTAC and related targeted protein degradation designs, this linker is used to connect two functional modules—such as an E3 ligase–binding moiety and a second ligand or reactive intermediate—by first installing thiol-reactive chemistry on each partner and then using the bifunctional maleimide to form a stable thioether linkage. Its short PEG3 segment helps balance flexibility and effective reach, which can improve productive ternary complex formation and thereby support degradation potency. The compound is therefore valuable for assembling degraders, optimizing linker length, and generating site-specific conjugates for structure–activity relationship studies.

Mal-NH-PEG3-NH-Mal

Structure of 1008402-47-8

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Category
PROTAC Linker
Molecular Formula
C₂₂H₃₀N₄O₉
Molecular Weight
494.50
Appearance
Waxy Solid

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

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Purity
>97%
Appearance
Waxy Solid
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
3-(2,5-dioxopyrrol-1-yl)-N-[2-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethoxy]ethyl]propanamide
Synonyms
Bis-Mal-PEG3; 3-(2,5-dioxopyrrol-1-yl)-N-[2-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethoxy]ethyl]propanamide
Boiling Point
791.7±60.0 °C at 760 mmHg
Density
1.319±0.1 g/cm3
InChI Key
KFEOJIBJOGJZDY-UHFFFAOYSA-N
InChI
InChI=1S/C22H30N4O9/c27-17(5-9-25-19(29)1-2-20(25)30)23-7-11-33-13-15-35-16-14-34-12-8-24-18(28)6-10-26-21(31)3-4-22(26)32/h1-4H,5-16H2,(H,23,27)(H,24,28)
SMILES
C1=CC(=O)N(C1=O)CCC(=O)NCCOCCOCCOCCNC(=O)CCN2C(=O)C=CC2=O

This PROTAC linker, Mal-NH-PEG3-NH-Mal, is a bifunctional polyethylene glycol–based module designed to connect two targeting or conjugation partners through maleimide chemistry. Its flexible PEG scaffold supports favorable spatial presentation and can improve conjugation efficiency in staged PROTAC assembly workflows. The maleimide termini enable selective coupling to thiol-bearing ligands under mild conditions, facilitating construction of targeted protein degraders. Detailed structural and reactivity considerations are provided below.

Structure: The linker contains a central PEG chain providing conformational flexibility, flanked by two maleimide groups connected via amide linkages. Maleimides feature electron-deficient alkene moieties that undergo thiol addition, while the PEG segment imparts hydrophilicity and improves solubility in aqueous media.

Reactivity: Maleimide groups react with thiols via a Michael-type addition, forming stable thioether adducts. Suitable conditions typically employ aqueous or mixed aqueous buffers at near-neutral pH, with thiol-containing partners generated or maintained in reduced form. Reaction rate and selectivity depend on thiol concentration and solvent composition; catalysts are generally unnecessary, but careful control of competing nucleophiles is recommended during PROTAC synthesis.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
g/mol
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