Cbz-N-amido-PEG3-acetic acid

 CAS No.: 462100-05-6  Cat No.: BP-501648  Purity: >98% 4.5  

Cbz-N-amido-PEG3-acetic acid is a PEG-based linker building block incorporating a carboxylic acid for conjugation and a PEG3 spacer that provides aqueous solubility and conformational flexibility. The Cbz group serves as a protected amine functionality, enabling controlled coupling to activated carboxylates or other electrophiles during PROTAC synthesis. In targeted protein degradation constructs, PEG linkers are commonly used to tune the spatial relationship between the ligand “warhead” and the E3-recruiting module, reducing steric clashes and helping maintain productive ternary complex formation. The acetic acid terminus allows straightforward attachment to neighboring fragments through amide bond formation, while the ether-rich chain can mitigate aggregation and improve handling in biochemical assays. This linker is therefore valuable for researchers optimizing linker length, polarity, and attachment chemistry in PROTAC design, facilitating systematic structure–activity studies and improving reproducibility of degradation experiments.

Cbz-N-amido-PEG3-acetic acid

Structure of 462100-05-6

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Category
PROTAC Linker
Molecular Formula
C₁₆H₂₃NO₇
Molecular Weight
341.36
Appearance
Viscous Liquid

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

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Purity
>98%
Appearance
Viscous Liquid
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-[2-[2-(phenylmethoxycarbonylamino)ethoxy]ethoxy]ethoxy]acetic acid
Synonyms
Cbz-9-amino-4,7-dioxanonanoic acid; Cbz-AEEEA
Boiling Point
512.8±50.0 °C at 760 mmHg
Density
1.217±0.1 g/cm3
InChI Key
DMBZCDPECWJRJR-UHFFFAOYSA-N
InChI
InChI=1S/C16H23NO7/c18-15(19)13-23-11-10-22-9-8-21-7-6-17-16(20)24-12-14-4-2-1-3-5-14/h1-5H,6-13H2,(H,17,20)(H,18,19)
SMILES
C1=CC=C(C=C1)COC(=O)NCCOCCOCCOCC(=O)O

Cbz-N-amido-PEG3-acetic acid is a PEG-based linker building block designed to support the modular synthesis of PROTACs by providing a flexible, hydrophilic spacer that can improve solubility and help tune the spatial relationship between the ligand-recruiting moiety and the target-binding element. Its Cbz-protected amino and carboxylic acid functionalities enable robust coupling strategies commonly used in targeted protein degradation workflows. The following sections describe its structure and practical reactivity considerations in detail.

Structure: The molecule contains a carbobenzyloxy (Cbz)-protected amino group, a short poly(ethylene glycol) segment, and a terminal acetic acid functionality. It features ether-rich PEG connectivity that confers conformational flexibility, together with a Cbz carbamate and a terminal carboxylic acid.

Reactivity: For PROTAC assembly, the carboxylic acid can be activated for amide bond formation using standard coupling chemistries (for example, carbodiimide/uronium activators) in compatible polar aprotic solvents. The Cbz group is typically retained during coupling and can be removed under hydrogenolysis conditions when deprotection is required. Mechanistically, activation promotes nucleophilic acyl substitution to install the desired linker-to-ligand amide connectivity.

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It is commonly abbreviated as: C1V1 = C2V2

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