Cbz-N-amido-PEG4-propionic acid

 CAS No.: 756526-00-8  Cat No.: BP-500429  Purity: >98% 4.5  

Cbz-N-amido-PEG4-propionic acid is a polyethylene glycol–based PROTAC linker building block incorporating a terminal propionic acid for carboxylate-mediated coupling and a PEG4 chain that provides aqueous solubility and conformational flexibility. The Cbz (benzyloxycarbonyl) group and the N-amido functionality enable controlled functionalization and serve as protected handles during multi-step synthesis, allowing researchers to attach this linker to either a ligand-bearing amine or an activated carboxylate partner under standard peptide-coupling conditions. In PROTAC architectures, PEG linkers are widely used to spatially separate the two binding modules, reduce steric clashes, and maintain productive geometry for recruiting the target protein and the E3 ligase. This compound is therefore valuable for constructing degraders that require reliable linker length and hydrophilicity, facilitating systematic structure–activity relationship studies and improving compatibility with common conjugation workflows.

Cbz-N-amido-PEG4-propionic acid

Structure of 756526-00-8

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Category
PROTAC Linker
Molecular Formula
C₁₉H₂₉NO₈
Molecular Weight
399.44
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
3-[2-[2-[2-[2-(phenylmethoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
Cbz-NH-PEG4-CH2CH2COOH; Cbz-N-amido-PEG4-acid; Cbz-NH-PEG4-propionic acid; Cbz-15-amino-4,7,10,13-tetraoxapentadecacanoic acid
Boiling Point
571.2±50.0 °C at 760 mmHg
Density
1.2±0.1 g/cm3
InChI Key
QGTQYXJCFILXDO-UHFFFAOYSA-N
InChI
InChI=1S/C19H29NO8/c21-18(22)6-8-24-10-12-26-14-15-27-13-11-25-9-7-20-19(23)28-16-17-4-2-1-3-5-17/h1-5H,6-16H2,(H,20,23)(H,21,22)
SMILES
C1=CC=C(C=C1)COC(=O)NCCOCCOCCOCCOCCC(=O)O

Cbz-N-amido-PEG4-propionic acid, provides a PEG-based hydrophilic spacer terminating in a carboxylic acid handle and a protected amide functionality. Its flexible polyether chain supports productive ternary-complex formation by reducing steric constraints and improving solubility in bioconjugation workflows. The Cbz-protected amine enables controlled coupling strategies, while the acid group supports stable linker attachment to targeting ligands or E3-recruiting moieties. Detailed structural and synthetic considerations are provided below.

Structure: The linker contains a poly(ethylene glycol) segment that confers flexibility and water compatibility, connected to a propionic acid terminus. An amide linkage and a carbamate (Cbz) protecting group define the core connectivity, with ester-like carbonyl environments that support stable conjugation chemistry.

Reactivity: The carboxylic acid can be activated for amide-bond formation using standard coupling protocols such as carbodiimide-based activation in polar aprotic solvents, often with an amine nucleophile on the partner ligand. The Cbz group is typically removed under hydrogenolysis conditions to reveal a primary amine for subsequent coupling. The PEG chain generally tolerates mild aqueous/organic mixtures, enabling stepwise assembly of PROTAC constructs through sequential protection, deprotection, and conjugation steps.

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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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