TCO-PEG3-acid

 CAS No.: 2141981-86-2  Cat No.: BP-501508  Purity: 95% 4.5  

TCO-PEG3-acid is a functionalized polyethylene glycol linker bearing a trans-cyclooctene (TCO) reactive handle and a terminal carboxylic acid, providing a short, flexible three–ethylene glycol unit for controlled spacing and improved solubility in PROTAC-related constructs. The TCO moiety is designed for rapid, bioorthogonal conjugation via inverse-electron-demand Diels–Alder chemistry with tetrazine-containing partners, enabling efficient installation of the linker between targeting ligands and other PROTAC components under mild conditions. The carboxylic acid end supports straightforward amide coupling or other carboxyl-derivatization strategies, facilitating attachment to activated carboxylates or amine-bearing fragments. In targeted protein degradation research, this linker helps tune the geometry and effective molarity of multicomponent assemblies, which can be critical for productive ternary complex formation and degradation potency. Its modular design supports systematic structure–activity studies and reliable synthesis of next-generation conjugates.

TCO-PEG3-acid

Structure of 2141981-86-2

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Category
PROTAC Linker
Molecular Formula
C₁₈H₃₁NO₇
Molecular Weight
373.44

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

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Purity
95%
Solubility
DMSO, DCM, DMF
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-[2-[2-[[(4Z)-cyclooct-4-en-1-yl]oxycarbonylamino]ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
1-(Cyclooct-4-en-1-yloxy)-1-oxo-5,8,11-trioxa-2-azatetradecan-14-oic acid; 3-(2-{2-[2-({[(4Z)-cyclooct-4-en-1-yloxy]carbonyl}amino)ethoxy]ethoxy}ethoxy)propanoic acid
InChI Key
LUXDTTWUFRONNF-UPHRSURJSA-N
InChI
InChI=1S/C18H31NO7/c20-17(21)8-10-23-12-14-25-15-13-24-11-9-19-18(22)26-16-6-4-2-1-3-5-7-16/h1-2,16H,3-15H2,(H,19,22)(H,20,21)/b2-1-
SMILES
C1CC=CCCC(C1)OC(=O)NCCOCCOCCOCCC(=O)O

TCO-PEG3-acid is a polyethylene glycol–based PROTAC linker acid designed to enable efficient conjugation of targeting ligands through a reactive trans-cyclooctene (TCO) handle. Its PEG spacer supports favorable solubility and conformational flexibility, which can improve productive ternary complex formation in targeted protein degradation workflows. The molecule is described in detail below, including structural features and practical guidance for PROTAC assembly and linker utilization.

Structure: The linker contains a PEG3 ethylene glycol chain terminating in a carboxylic acid, providing hydrophilicity and a handle for amide formation. It incorporates a TCO moiety, featuring a strained cyclooctene framework capable of rapid bioorthogonal reactivity. The structure includes ether linkages and an acid functional group.

Reactivity: The carboxylic acid enables standard coupling chemistries to attach PROTAC partners via amide bond formation, typically using carbodiimide-based activators and an amine-containing ligand under controlled pH. The TCO functionality is commonly used in inverse-electron-demand cycloaddition with tetrazines, proceeding via strain-promoted cycloaddition. Reactions are generally performed in compatible organic solvents or aqueous buffers that preserve TCO integrity, with purification to remove unreacted components.

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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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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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