Azido-PEG3-maleimide

Name: Azido-PEG3-maleimide
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 1858264-36-4

Cat No.: BP-500130

Purity: >98.0% 4.5

Azido-PEG3-maleimide is a heterobifunctional PEG-based linker that combines a terminal azide handle with a maleimide electrophile, enabling two orthogonal conjugation chemistries in PROTAC construction. The short PEG3 spacer provides aqueous solubility and conformational flexibility, while the maleimide group reacts selectively with thiols (e.g., cysteine-containing ligands or engineered protein/peptide handles) to form a stable thioether linkage. In parallel, the azide functionality can be used for bioorthogonal azide–alkyne cycloaddition (Cu-free strain-promoted variants) or related click strategies to attach a complementary component such as a second targeting ligand, warhead, or reporter. In targeted protein degradation research, this linker is valuable for assembling modular PROTACs with controlled geometry, facilitating efficient coupling of ligand fragments under mild conditions and supporting systematic structure–activity relationship studies. Its dual-reactivity helps streamline synthesis and improves the reproducibility of multicomponent conjugates.

Structure of 1858264-36-4

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Category

PROTAC Linker

Molecular Formula

C15H23N5O6

Molecular Weight

369.37

Appearance

Solid

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

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Purity

>98.0%

Solubility

10 mm in DMSO

Appearance

Solid

ShelfLife

0-4°C for short term (days to weeks), or -20°C for long term (months).

Storage

Store at -20 °C, keep in dry and avoid sunlight.

Shipping

Room temperature

IUPACName

N-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl]-3-(2,5-dioxopyrrol-1-yl)propanamide

Synonyms

Azido-PEG3-Maleimide Kit;N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamide

InChI Key

OGSSEPXEBBNVGN-UHFFFAOYSA-N

InChI

InChI=1S/C15H23N5O6/c16-19-18-5-8-25-10-12-26-11-9-24-7-4-17-13(21)3-6-20-14(22)1-2-15(20)23/h1-2H,3-12H2,(H,17,21)

SMILES

C1=CC(=O)N(C1=O)CCC(=O)NCCOCCOCCOCCN=[N+]=[N-]

1. Detection of proteolytic activity by covalent tethering of fluorogenic substrates in zymogram gels

Ameya A Deshmukh, Jessica L Weist, Jennifer L Leight Biotechniques. 2018 May;64(5):203-210. doi: 10.2144/btn-2018-0005.

Current zymographic techniques detect only a subset of known proteases due to the limited number of native proteins that have been optimized for incorporation into polyacrylamide gels. To address this limitation, we have developed a technique to covalently incorporate fluorescently labeled, protease-sensitive peptides using an azido-PEG3-maleimide crosslinker. Peptides incorporated into gels enabled measurement of MMP-2, -9, -14, and bacterial collagenase. Sensitivity analysis demonstrated that use of peptide functionalized gels could surpass detection limits of current techniques. Finally, electrophoresis of conditioned media from cultured cells resulted in the appearance of several proteolytic bands, some of which were undetectable by gelatin zymography. Taken together, these results demonstrate that covalent incorporation of fluorescent substrates can greatly expand the library of detectable proteases using zymographic techniques.

Azido-PEG3-maleimide is a versatile heterobifunctional PROTAC linker combining an azide handle with a maleimide electrophile for orthogonal conjugation. Its polyethylene glycol segment provides conformational flexibility and improved aqueous compatibility, supporting efficient assembly of targeted protein degraders. The dual-reactivity design enables stepwise attachment of ligands under mild conditions, facilitating modular PROTAC synthesis. Detailed structural and reactivity considerations are provided below.

Structure: The linker contains a polyethylene glycol spacer terminated by an azide group and a maleimide moiety. It features an electrophilic maleimide double bond suitable for Michael-type addition and an azide suitable for bioorthogonal click chemistry. The PEG segment imparts hydrophilicity and conformational mobility in aqueous media.

Reactivity: The maleimide typically reacts with thiols via a Michael addition under mildly basic aqueous conditions, often using fresh thiol-containing partners to minimize side reactions. The azide enables azide–alkyne cycloaddition for orthogonal conjugation, commonly employing copper-free or copper-catalyzed variants depending on substrate compatibility. Standard PROTAC assembly workflows use buffered solvents such as aqueous organic mixtures, with temperature and pH tuned to preserve ligand integrity and maximize coupling efficiency.

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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