TCO-PEG9-maleimide

Name: TCO-PEG9-maleimide
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 2183440-37-9

Cat No.: BP-500198

Purity: 95% 4.5

TCO-PEG9-maleimide is a bifunctional, polyethylene glycol–based linker that combines a trans-cyclooctene (TCO) moiety with a maleimide group for efficient conjugation chemistry. Structurally, it features a flexible PEG chain of intermediate length that separates the reactive termini, improving accessibility and reducing steric hindrance during bioconjugation. In PROTAC and related targeted degradation designs, the TCO handle enables rapid and selective ligation to tetrazine-bearing partners via an inverse-electron-demand Diels–Alder reaction, providing a robust way to assemble or exchange molecular components under mild conditions. The maleimide group, in turn, reacts selectively with thiols (e.g., cysteine residues or thiol-containing linkers) to install the linker onto protein ligands, antibodies, or engineered scaffolds. This combination makes TCO-PEG9-maleimide valuable for constructing modular, site-specific conjugates and for optimizing spatial orientation in ternary-complex formation, thereby supporting systematic studies of targeted protein degradation efficiency.

Structure of 2183440-37-9

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Category

PROTAC Linker

Molecular Formula

C₃₆H₆₁N₃O₁₄

Molecular Weight

759.88

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

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Purity

95%

Solubility

DMSO, DMF, DCM

Storage

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

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

[(4Z)-cyclooct-4-en-1-yl] N-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl]carbamate

Synonyms

(Z)-Cyclooct-4-en-1-yl (33-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-31-oxo-3,6,9,12,15,18,21,24,27-nonaoxa-30-azatritriacontyl)carbamate; (4Z)-cyclooct-4-en-1-yl N-{29-[3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamido]-3,6,9,12,15,18,21,24,27-nonaoxanonacosan-1-yl}carbamate; (E)-Cyclooct-4-en-1-yl (33-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-31-oxo-3,6,9,12,15,18,21,24,27-nonaoxa-30-azatritriacontyl)carbamate

InChI Key

TZGDGNPQUCQZSR-UPHRSURJSA-N

InChI

InChI=1S/C36H61N3O14/c40-33(10-13-39-34(41)8-9-35(39)42)37-11-14-44-16-18-46-20-22-48-24-26-50-28-30-52-31-29-51-27-25-49-23-21-47-19-17-45-15-12-38-36(43)53-32-6-4-2-1-3-5-7-32/h1-2,8-9,32H,3-7,10-31H2,(H,37,40)(H,38,43)/b2-1-

SMILES

C1CC=CCCC(C1)OC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCOCCNC(=O)CCN2C(=O)C=CC2=O

TCO-PEG9-maleimide is a bifunctional PROTAC linker designed to connect a targeting ligand to a second binding element through a stable PEG-based spacer and a maleimide handle. Its trans-cyclooctene (TCO) functionality supports efficient bioorthogonal conjugation, while the maleimide enables selective coupling to thiol-containing partners. These features make it particularly useful for assembling PROTAC constructs with controlled geometry, improved solubility, and reliable modular synthesis; detailed structural and reactivity considerations are provided below.

Structure: The molecule combines a PEG spacer with a maleimide electrophile and a trans-cyclooctene moiety. It contains an activated cyclic imide for thiol capture and a strained alkene suited for rapid inverse-electron-demand cycloaddition. The ether-rich PEG segment confers flexibility and enhanced hydrophilicity.

Reactivity: The maleimide group reacts with free thiols via a Michael-type addition under mildly basic aqueous conditions, forming a stable thioether linkage suitable for stepwise PROTAC assembly. The TCO handle is compatible with bioorthogonal conjugation strategies that rely on fast, selective ligation to appropriate tetrazine partners. Typical workflows use buffered aqueous solvents, with careful control of thiol availability and avoidance of competing nucleophiles.

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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