DBCO-NHCO-PEG2-maleimide

Name: DBCO-NHCO-PEG2-maleimide
Brand: BOC Sciences
Rating: 5 (1 reviews)

Cat No.: BP-502066 4.5

DBCO-NHCO-PEG2-maleimide is a bifunctional, PEG-based chemical linker designed for copper-free click conjugation and subsequent thiol-reactive coupling. Structurally, it incorporates a dibenzocyclooctyne (DBCO) moiety for strain-promoted azide–alkyne cycloaddition, an amide-linked PEG spacer of short chain length to provide aqueous solubility and controlled distance, and a terminal maleimide group that reacts selectively with cysteine or thiol-containing ligands to form stable thioether linkages. In PROTAC and targeted degradation workflows, this type of linker enables modular assembly by first coupling an azide-bearing component (e.g., a warhead or targeting ligand) to the DBCO handle, then attaching a second component through maleimide–thiol chemistry, thereby positioning functional groups to support productive ternary complex formation. Its value lies in facilitating reliable, stepwise conjugation under mild conditions, improving experimental flexibility when optimizing linker length and geometry for degradation efficiency.

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Category

PROTAC Linker

Molecular Formula

C₃₂H₃₄N₄O₇

Molecular Weight

586.63

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

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Please store the product under the recommended conditions in the Certificate of Analysis.

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Room temperature in continental US; may vary elsewhere.

IUPACName

N-[2-[2-[3-[[3-(2-azatricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl)-3-oxopropyl]amino]-3-oxopropoxy]ethoxy]ethyl]-3-(2,5-dioxopyrrol-1-yl)propanamide

InChI Key

RNZYXLRPJHTQSV-UHFFFAOYSA-N

InChI

InChI=1S/C32H34N4O7/c37-28(14-18-35-30(39)11-12-31(35)40)34-17-20-43-22-21-42-19-15-29(38)33-16-13-32(41)36-23-26-7-2-1-5-24(26)9-10-25-6-3-4-8-27(25)36/h1-8,11-12H,13-23H2,(H,33,38)(H,34,37)

SMILES

C1C2=CC=CC=C2C#CC3=CC=CC=C3N1C(=O)CCNC(=O)CCOCCOCCNC(=O)CCN4C(=O)C=CC4=O

This DBCO-NHCO-PEG2-maleimide linker is designed for modular assembly of PROTAC constructs, enabling efficient conjugation between thiol-bearing targeting ligands and azide/alkyne-functional partners. Its orthogonal chemistries support selective coupling under mild conditions, helping preserve sensitive binding motifs and improve overall synthetic flexibility. The structure and reactivity features that follow describe how this linker participates in PROTAC-relevant conjugation workflows in detail.

Structure: The linker contains a DBCO cyclooctyne handle for copper-free azide–alkyne cycloaddition, a maleimide electrophile for thiol addition, and a PEG spacer that provides aqueous compatibility and conformational flexibility. It includes an amide linkage connecting functional segments, supporting stable covalent attachment during synthesis.

Reactivity: The maleimide group reacts with thiols via Michael-type addition, typically performed in aqueous or mixed aqueous buffers at conditions that maintain thiol nucleophilicity while limiting side reactions. The DBCO moiety enables strain-promoted cycloaddition with azides without copper catalysis. For PROTAC assembly, sequential or orthogonal conjugation strategies can be used to attach targeting ligands while minimizing cross-reactivity.

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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